Some things I noticed while playing:
Why are these two roofs accessible, but the other one isn't? As a scout this bugged me, since it looks like you can just hop on over to it like the others, but then NOPE PLAYERCLIP. Either let players walk on it, or provide visual feedback showing it's blocked off (fence, railing, etc).
I'd say change the middle post holding up the saws to be bent like the others, so that most players can't get on the roof, because...
As you can see, snipers get too good a view of the enemy spawn. And an engineer with a wrangled level 3 up here would also wreck shit. also there's a little visible nodraw up there in the corner that I only just noticed.
This indoor area immediately outside blu spawn looks like it should be func_respawnroom'd, but it isn't. Also, this window is very misleading - it's solid, but looks like you can shoot through it. I'd suggest using a different window model that has glass.
This area is very cool, but unfortunately I
never once got to go inside it. Why? I was on blu, and the attackers are funneled into a small chokepoint with no flanking routes - these three doors in the center. They're practically all on top of each other, making it very easy for red to keep the enemy team out. I'd highly suggest adding in a flanking route along the side, so that scouts, spies, and other soft classes that rely on ambushes can worm their way in. Maybe have it in the upper area to the left in the picture?
This lower area is fairly useless. It provides interesting vertical gameplay, but serves no purpose -
why should anyone go down there? To pick up a medium ammo pack? Red team won't, because if they need metal/ammo they can run into spawn. Blu team won't because it's probably not a big enough reward for the risk, and they won't be setting up a base there anyway. I would suggest maybe extending the ledge and making a flanking route (as mentioned previously) for the attackers that leads down here. Or at least make it into a health pack. It seems fairly easy to fall into the bottomless pit from here, so it might be worth it to make it into a full health pack, as a reward for the risk. This screenshot also shows how dreadfully close the red spawn is not only to this arena, but to the cart's track. If we had ever gotten the cart that far along, we'd never had been able to push it past there, since soon as someone spawns they'd be on top of us.
Recap:
-need more consistency on roof access
-keep snipers/engies/etc off roofs
-func_respawnroom outside blu spawn, and change window
-last area is way too chokepointy for attackers, give them an easier way in.
-lower path in the hole serves no real purpose
Also, is there any way to access the second half of the map before the first three points are capped? You should give access to them so that red can get setup there before blu arrives. I'd mention the sightlines and lack of cover between points 2 and 3, but that's been pointed out plenty.