Sounds like you had fun!
OK, crits if you want em, in order of the new screenshots.
1) There are still too many windows on this building, and the structure itself is not that exciting. Why not push some areas of the building out, to stagger the sides a bit so they're not flat? As an example, check out this image from the No More Room in Hell mod by dark:
Less flat, more of that ^ = nice.
2) The decal seems oddly placed. Too high and overlapping with the windows. I'd move it down and to the right, over to the side of the building away from the windows. Maybe add some trim or signs of a real doorway?
3) The hill does look nice. I was pleasantly surprised to see you curved it instead of just angled it up, so it does look more natural. As for the building though, I'd expect the windows to not be so close to the ground. Perhaps some cement areas near the base of the building before it turns into plastery looking wall with windows. Additionally, there's a whole lot of concrete between the sidewalk and the buildings, looking strange. I'd expect either grass between the sidewalk and the building or at least dirt or a driveway or something to lend the area more variety.
4) Where did all the rubble come from? It looks nice, but doesn't make too much sense. Maybe if the walls around it were concrete instead of plaster, or if the roof above was cut up and you could see where the concrete broke off from it would look more realistic.
5) I'd like to get up here with a crossbow. Also, its a shame about the glowing props over near the parking lot. It seems like the closer light posts are lit correctly, but the further ones aren't (along with the 'crete barriers). Any way to fix that? Also, are you planning on adding traffic lights to your brushwork?
6) The hill looks really nice in that shot! I also like the destroyed windows. You could probably put some rubble down near the ground below those windows. I wish the building itself was less boxy. Also Why not make the bottom parts of the building (without windows on the slope) brick, or something that looks more like a building foundation?
7) Ah, the building up top looks good. It has more interesting geometry, and you've textured in a foundation below the windows. Still quite a few windows on the left side though.
8) Did the treehouse get used much in the playtests?
9) Missing texture on the right side of the cream building directly across from the camp spot.
10) Given the height of the first floor in that building, the windows on the second floor make no sense. The bottom of the window is literally on the edge with the top of the door. I'd just get rid of the windows on that level entirely.
11) I like the blasted hole on the left. How's the performance from that part of the map? I imagine the whole thing is pretty much being rendered at once.
12) midkay +1 frag
13) Playground seems sparse and unused. Why not add a few more props and blend in some dirt around them, making the park look like kids have run around so much in it that the grass has died in spots.
14) Not much to say about this one, just I'd like to see some shots of the inside of that area, with all the rubble and the stairs.
Any ideas for replacing the combine wall? How's the performance of the map overall? Do you have a soundscape yet?
Seems like you could stand to dirty the map up a bit, with decals, overlays, random props and debris.
If you don't have time to read anything else, read this: If you're curious about ways to make your buildings look better, fire up HL2 and walk around the outside of the train station. Snap screenshots of each building, and look at them, study them. I wouldn't suggest lifting the exact design, but instead identify some architectural elements (like rounded edges, varied roof heights, extruded wall geometry etc) and use them in your map. It'll also give you an idea of how Valve implemented the textures you're now using.
Looking forward to more. I also feel like such a backseat mapper right now. Feel free to discard comments or suggestions as you see fit.
