Well, take this feedback with a grain of salt because I am still a novice mapmaker.
I understand the desire to make a remake map, and for anyone that has played it, the TF2 version of Dust2 has some fun moments. The reason for this of course is that Dust went through years of refinements and is a very well balanced fighting space with lots of alternative paths.
Maybe my problems with your map arise because I never played crackhouse. To me it seems like there are too few ways to get inside the red base, and additionally that the overall size of the map is really small. A single sniper on top of the blue base would be able to lock down most of the map, and easily retreat to safety. In fact I think a turret on either roof would be able to hit most of the map. Now in one sense this is fine, but what I predict will happen, is that all of the red team will be stuck inside their base for the duration.
If you think about it, once the turrets are down, a scout could get inside red base, grab the intel, run out and cap it in what, 10 seconds? 15? If everyone was the same class, or very few people were playing, I could see this being somewhat enjoyable overall, but with 24 people in TF2 I can't imagine having any fun on this map.
Now to aesthetics. Your cubemaps are detailed, I especially like the pool with reflective sides, a neat effect. However I'm not sure why the city street would be reflective, seems odd. Also the city street/cars are close enough that you can see they are off of the ground, ruined, and no one is driving. The buildings and doors look good. The awnings seem a little small and those windows are causing shadows which seem out of place.
Some of this may seem harsh but my goal was to give some good constructive feedback for you
