Looks:
Nice work on the bottom, it's easy to connect that you've done many trench war looks. Then when you see the top route, there the looks aren't even close to level of bottom.
Circle modeled polyislands don't look as interesting as more cornerous ones, in addition circle modeled polyislands can't be polybugfixed so it's worse in gamewize too.
Also now that you got roof/edges in your map, you could also make roof/edges good looking. Lazy/easy solution is to set black fade everywhere (not only bottom and half of the left edge like in this case).
The another more preferable solution is to work more with polygons and make them good looking at outside of playground too, check for example ctf_Steel, there's the outside is good looking with very simplistic polywork.
Not saying that this top looks bad, it's playable but boring.
HTF gameplay:
Alright map, I guess there are some tactical stuff at bases. The main issue I see is that once I get the flag, I'd go camp under that OPC (only player collide) poly and make it extremely annoying for attackers to try steal the flag.
Two things that I'd improve:
- delete the opc polygon, it's just harming the play
- set team spawns into other place than the best camping place for flagger
