Plains of Snow
Surely the most popular of all the maps, certainly for those who played in leagues, very evenly balanced map(relatively speaking, war2 had no completely balanced maps originally) which allowed easy wall-in and required quick expansion due to the 40K mines which disappeared very quickly.
As with most 8 player maps, it wasnt the best for one vs one, but was much better for team play, unfortunately some people played this and nothing else, and when you finally managed to drag them off it and beat them on another map, you'd always get the classic line "Come on, rematch, Plains of Snow!"
When Kali MPX was in its heyday, the best games we would organize would be 4v4. We wouldnt organize teams, just decide it was left vs right, so it was luck of the draw who was on your side, you'd just message everyone with "left" or "right" at the start of the game and see who to team up with. Given all the mines were taken, if a rush didnt work the only way to expand was to chop through the trees in the middle or top/bottom mines. This made for some cracking games where every piece of gold was vital and every unit scarce.
Love it or hate it, you had to play this map if you wanted to mix it with everyone, I went through periods of loving it, then throroughly disliking it, to getting bored of it, certainly in one vs one games, however it certainly left its mark, hence its resurrection in Warcraft 3.

Garden of War
My personal favourite, the first map I ever played online on Kali Central in early 1996 and remained a favourite despite that game ( I was bottom right, and got towered -talk about a baptism of fire lol).
Sure it was inbalanced, if you got the 7:00 position you were screwed, you either had to move or chop a piece of wood before you could build your hall so you got well behind, but hey thats what team mates were for!
Few wall-in opportunities meant you never know what you were going to do or how you were going to build until you found out your starting position. Like Pos, it wasnt really a good choice for head to head matches, but in team games it really came into its own.
Like most players, ive had some huge games on GOW, with some unbelievable stats at the end. I could happily spend an entire evening playing only team games on GOW, (sometimes did) but rarely got bored of it, due its variety.
I was never one of those people who rushed for the centre, sure there was tons of gold there, but no room to build stuff once you had towered in, there were plenty of spots to expand to at the edge of the map, and easier to protect as they didnt have four entrances, plus the centre mines could be deatch and decayed from over the trees at each side - I cant remember ever losing to a team that grabbed the centre at the start, still it used to panic me when they did :)
The only downside to the map was the poor unit pathing in War2 meant units often got lost and ended up in dead ends when moving them long distances.
A truly classic map, again made its way into War3, however not as one of the bnet maps randomly chosen for team games.

One way in, one way out.
When I first started playing in OZWL (Australian Warcraft League) this was the most popular head to head map. Most maps with just the two starting positions tend to be popular as they eliminate the need for scouting to find your enemy, allowing you to concentrate on amassing your army as quick as possilble. This is a shame, as scouting is a part of all RTS games, however I must admit I did enjoy playing on this map for a while.
One thing that this map was good for practising was the rush. I was a pretty useful rusher for a while, and most of the games on here rarely lasted more than a few minutes, however some were very even and went on for a while, still with only 6 mines on the map, it was never going to lead to long games.
Wall-in strategies were devised to stop rushing, and you could place your men at such a point at the entrance to set up several 3v1 and 5v3 battles to allow you to build up while sacrificing minimal amounts of men. Tactics like this lead to the longevity of this map's popularity, and will go down as one of my all time favourites, though I preferred team games.
The main imbalance was that the top player could blizzard peons at the bottom player's second mine, but as games often didnt get that far, it wasnt much of a problem.

Death in the middle
This was an immensely popular map for both 1v1 and 2v2, despite a huge imbalance to one player who had to have his hall miles from the mine because of the way the trees were laid out (I forget which starting position this was). However a fixed version of the map soon came out.
Death in the middle was a bit of a misnomer, as battles rarely happened in the wide open space in the middle, people rarely attack at exactly the same time, so the death occurred amongst the maze of trees surrounding each base.
Like one way in/out(above) a 2v2 on this map negated the need to scout for your enemy, but as it was a relatively small map, if you were attacked your ally didnt have far to come to help.Another bonus was a natural expansion spot that was easily defended, so if initial rushes were held off, games of decent length ensued. It was always fun sappering through the rock of people who towered their bases and longing to see the look on their face when you waltzed your fatties into their town :).

Fierce Ocean Combat
I used to love sea maps, I became a much better player on sea than i was on land, mostly due to the fact that most people avoided sea like the plague - hence my disdain for the POS mongers.
War2 had sea, it was part of the game so why not learn it? It certainly extended my interest in war2 with a whole new avenue of units and strategies that those landlubbers never got to use :)
FOC was my favourite sea map, though to be fair there werent that many playable sea maps of any size, apart from High Seas Combat, which wasnt a proper sea map anyway:) (explanation provided in that maps text ).
Given the size of the mines (50K i think), and only one mine per island, you had to expand, so you had to build boats, whether you just expanded with trannies for an invasion force, or build a naval force and dominate the sea was always a tough choice. I tended to go for the naval force as you had more control over the map, though i did used to enjoy games where i had lost the sea but expanded a couple of times and used wizards to protect my shipyards.
Again, not a terrifically well balanced map, you could get hit from the sea on some islands, while others you were sheltered, but a terrific multiplayer map (maybe not 4v4 though, only 1 mine per island) 2v2 and 3v3 were the best combo's on FOC.
I still like to pop onto BNET now and then and play war2 if there are any people around, and i usually choose this map, and even after all these years, its surprising how few people are able to play on sea. tut tut.

The Spiral
This was a fantastic map that was probably the most interesting sea map, certainly for one v one games. The large amount of land and the extra mine on each island, plus the closeness of islands to each other meant a ground force was necessary as well as boats. In fact, boats were far less effective as the narrow channels between islands meant jugs were easily dealt with by wizards.
With an odd number of islands, it meant a battle for empty island if it was a 2v2, or a quick island invasion without having to scout knowing there was a 2 in 3 chance you would land on your enemies island.
One of the best games I ever played was on this map, against Umgah, one of Ozwl's top players and a superb sea player to boot. I was human against his orc, and i was the aggressor the whole game, i took the sea but his defence of his land against my invasions and jugs was impressive, finally it came down to a battle to secure the final island as we each had mined out two each - a battle which unfortunaly he won so he ended the game the victor - still it was a fine game that mustve lasted 90 minutes.
I rarely had a quick game on this map, and had very few i didnt enjoy.

No way out of this maze
I couldnt imagine anything worse than a one v one on this map, but as a team map it was a lot of fun, even if it was a right pain in the ass to move around. For this reason, early rushes were not so common as it took half the night just to scout the other starting positions and a lot of micro to ensure your grunt/footman didnt get caught in a dead end.
However as the game went on and wood was chopped away, it would become easier, and due to the aforementioned difficulty in scouting, it was much easier to get away with an early expansion so lots of heavy land or air battles usually ended up on this map.
I didnt really have any preferred starting position, they were all fairly equal, it was just vital you were near your ally, or else it was too difficult to help or be helped effectively. Some people liked this map, some didnt.
I liked it. I liked it alot.

Friends
One of the few decent things to come out of the War2 expansion pack was this map. Blizzard made a ton of maps for the expansion set, and this solitary gem was the only one they needed to have bothered with. I think they must have commissioned a local kindergarten to design most of the others.
The (then) unique idea of having allies start around the same huge gold mine gave a new dimension to team play, and i've had many fun games on friends, including one which was the best game i ever played (see battle reports).
It was really a rusher's paradise, and not easy to wall in, though on high resources, an early rush could be fended off easily enough, and with plenty of room to build, a second hall gave rise to quick teching and huge ogre battles.
With such a huge mine to start with, games rarely required an expansion, but those that did were colossal battles.
Starting next to your ally was practically like having shared vision of their base which was what made this map such fun and so unique.

High Seas Combat
Not one of my favourite maps, but a popular one nonetheless, most notably for the invention of the foundry hop, which allowed players to expand on this sea map without building sea units. This technique negated the need for a large naval force, though at 6:00 you could easily get jugged if it was your starting base.
Once everyone knew about the foundry hop, most battles on here ended up as air battles, and the strat on this map was how to build dragons/gryphons as quickly as possible.
Rubbish one v one map, but half decent team map.

Nowhere to run, nowhere to hide
A real speciality map. Not one i indulged in that often but the unique nature of this map made it a popular one. Entire tournaments were staged around this map, tons of strategies were invented and re-invented as people continued to strive to achieve the best tactics and build orders.
NWTR was on a planet of its own, though you could hardly fly by the seat of your pants on this one, you had to know what you were going to do before the game started.
Not so much a map more of an equation.

Bridge to Bridge Combat
Another popular 8 player map, like No way out of this maze, it was a pain in the ass to move around, but there were plenty of mines, though the starting spots were a little cramped. The bridges could be defended easily enough with towers, but you were constantly moving around due to the need to constantly expand.
Popularity for this map seemed to wane as people played more POS and GOW, but i had a few decent 3v3 and 4v4 games on here.

3vs3
Another decent expansion set pud. I went through a period of playing this alot with Das and Hoog, I dont think we lost many at all. As you were walled in with trees, it totally negated the grunt rush, so by the time you could get to the enemy, you had a much higher tech. People often made the mistake of rushing to dragons/gryphons, the tree walls werent that thick and if you wanted to you could chop through to the enemy pretty quickly so you really needed a ground attack. Each base had a natural expansion, and the game varied greatly depending on whether you and your allies started next to each other not. This was very popular on Kali for a while after the expansion set came out.
A fun map with lots of interesting possibilities, i enjoyed playing this alot.

Islands in the stream
One of those maps you played when you were bored of the standard fare. Hard to start a game with it on Kali Central, but a nice map to play between friends. Excellent as a 2v2, with the possibility of one or both of you starting on an island. Again, the dynamics of this situation gave rise to some interesting games, but definitely one you had to play for fun, I couldnt imagine league players bothering with this one "waaaah, you only won cuz you had the main land bit - not fair".

The four corners
Probably the most balanced map due to its symmetry, but another I didnt care for much. There wasnt much in the way of lumber close to your hall, and the stupid paths on each island restricted you to where you could build stuff. Still, it was a departure from the mainstream, you had to get transports as there wasnt enough gold to effectively mount an air attack, unless you were playing noobs.

A continent to explore
For decent 3v3 and 4v4 matches you were fairly restricted if you fancied something different. I used to like playing on this, unless you were the poor bastard stuck in the middle. You knew you had to defend him if he was your team mate, if he wasnt youd go all out to nail him. If it was you, you prayed :). Still dont know to this day why blizzard put so many oil patches on this map.
Some starting spots were difficult to build an effective base layout with the ice and trees, but 2 evenly matched teams could have a decent game on this map, as the expansions were wide open, wall-ins werent really possible.

Mysterious Dragon Isle
This was played alot when I first got onto MPX and joined ozwl, it made a change from GOW and POS, but i didnt really like this one at all. There were plenty of far better maps.
The starting spots sucked, and there wasnt enough lumber to have a long game.
It may have looked like a dragon, but the only mystery to it was why anyone played it in the first place.

Cross the streams
Strategies on small maps are often limited, this one broke the mould. Like NWTR, it boiled down to using the strategy you decided on before the game started, however there were lots to choose from, and being a sea map only added to the mix.
I could never make up my mind about this one, it was certainly better than x-marks the spot, but even after all these years the jury's still out for me.
Another one where tons of map specific strategies were devised and executed. People had fun with it, which in the end is all that matters.

Gold seperates east from west
Why is this here? Its the screw-up map. You played this when you screwed up. Confused? Well its like this....
Gold Seperates was always the default map listed in the drop down list of available maps when you were creating your game. Sometimes you would forget to select certain things, random order, resources, or the map you wanted to play. When the latter occurred, you were given this map as default. Therefore when the game screen came up, in gold writing at the bottom was "gold seperates east from west" which roughly translated means "you screwed up and forgot to select the map, jerk".
That's whay its the screw-up map. No one ever chose it deliberately, it sucked.

X-marks the spot
Crap, rubbish, ruinous and hopeless. This map ruined OZWL as once it was discovered and the killer strat devised, everyone wanted to play it. Why not? quick games, lots of points if you knew the strategy and soon everyone did so it became a lottery.
Scissors, paper, rock anyone?