As a fan of CTF looking forward to seeing this on an imp, I'll leave this here.
In the meantime, I'll fly around it a bit and come back with some initial feedback.
---
EDIT: I have flown around the map as well as bombed around as Demoman in it. I hate to sound overwhelmingly negative, but while it's a really cool map, it needs a *lot* of work.
POSITIVES:
Mid being sunken in, plus the smorgasbord of route options leading to and from Mid, offers some nice gameplay. It honestly sounds like good fun to just slug it out in what is essentially a death pit.
Side routes on Mid have potential, and the "wraparound" areas lead to a flank with some nice height advantage on the defending team, though defenders have no way to climb up there without explosives or building jumps. Too bad the small alcove in them doesn't have any health/ammo, Demos can sticky jump in there for some sneakybombing and may need to restock.
Buildings in front of spawn exit are nicely designed, though a few gameplay tweaks could make them even better.
NEGATIVES:
Unacceptably dark in some areas. A few prop lights and the light_env just aren't lighting the map enough.
No info_observer_point entities?! Dude, wtf. Plonk a few of those in, point 'em where the fightin' happens, team-code ones pointing at Intel and spawn, and set the center one as a welcome point.
Missing/insufficient/misleading signage ("BATTLEMENTS" comes to mind, and the lack of signs for resupply)
I found a texture error and a place where I run into the skybox.
So many unjumpable roofs without indication that they are unjumpable.
Capture Zone/Intelligence: a bit too little cover from one angle and a bit too much cover from the other.
Too little cover for potential Sentry positions on the Intelligence.
Battlements have too little cover, they're way out in the open, and are fall-damage high
So many useless dead ends! What purpose do these have?!
Can we please have more than one exit out of spawn? I can easily see the spawn being camped by an attacker going for the flag, there's a sightline directly connecting these two points.
Speaking of that sightline, every single possible route with the Intellgence goes past that same point with a direct line of sight to respawning defenders, opening anyone trying to steal it to Demospam or a sentry parked there for days. It's like that spot in 2fort that covers both the L-shaft and the spiral.
All in all, there's some nice height variation, but the varying heights themselves are overscaled.
ALTERATIONS:
That small antechamber just ahead of spawn with the full ammo/small health should have a staircase to the lower level (that leads to Mid) in it, maybe delete the entrance leading to spawn to make spawncamping harder.
A small roof over the Intelligence area for Engineers to build under. As it stands, Demospam can wreck some of the key areas in the map.
Cut out half of that wooden fence prop and let us crouch-jump with the Intel onto that little ledge - trade speed for cover. Should also open up potential flanks against any Sentries parked there.
Either delete that useless, dark, dead-end chamber accessed by turning right out of spawn, or give it some purpose. Probably defensive purpose, this map seems a bit attack-oriented. I know CTF is normally a turtlefest, but this just seems like overcorrection.