Wow, I just found my first try on TF2 and it was in december 2007. I started maps on tf2 just after the release of the game but my first finished map was the artpass...
Perhaps this might inspire someone, but there was a period of time where I was doing these little speed-drawings by hand. These are inked and markered - no sketching involved.
Having taken courses in veil landscape painting (which isn't digital as you done it, but the concepts are the same), you'll want to flatten and straighten out the layers that head off into the linear perspective horizon. (You can still have cliffs on the first layer (the furthest one), but the bumps need to be a lot smoother as the human eye cannot perceive detail at that distance)
That layer also needs to be brought down a bit. You can tell it is awkward by the steep incline your power polls and its associated connectors need to take between layers 1 and 2.
Otherwise, it looks great. Love the TF2 symbol sun. Good show, sir!