This may be complicated and hard to implement, but...

[Riftoff]

I had an idea for the server today. From what I remember of being a 24/7 2FORT INSTANT RESPAWN noob, the main reason for me not being interested in custom maps was not the wait required to download the map (Warpath was the second TF2 map I ever played), but was general disinterest in knowing I probably wasn't going to like the map as much as I would like my favorite stock map. So I thought why not have a little indicator pop up when the map is about to change that explains the map and what stock map it is most similar too?

[captainAngry]

I don't think that is really possible. If I find anything, I will add it.

The downloads are pretty fast, and since all the maps are posted on the forum before they hit the server, you could even download them ahead of time.