For CSS specific entities, pretty much all you need are the CT/T spawns inside buyzones, and brushes for your hostage rescue points or bomb sites. Since everyone buys their weapons, you don't need to worry about weapon and ammo placement (or health placement).
I came across something that sped up my compile time a lot. Part of my map contained a large car park, and there were several dozen concrete bollards. Most of these were hex-based cones (it was mapped from a real place). They were all 1 unit off the ground to avoid splitting up the ground texture. It was taking 32 hours to compile on a 3GHz PC. Then I changed them all to func_wall entities and the compile time dropped to 41 minutes on a 2.4GHz PC.
Edit: Oh yeah, adding to what Leperous wrote, I ran the map in spectator mode and zoomed out so I could see the whole thing. Then I took a screenshot and printed it. Now when I come across a problem like a gap in a wall or an incorrect texture, I mark it on the map and write a small note next to it. I never remember the details once I'm back in Hammer.