A while ago, the 4th TF2Maps.net 72 Hour Mapping Contest ran. I went and made a 72 hour 5CP map alongside many others.
The map is called cp_derecho, based off of the (pending) theme of a storm front, and a type of wind storm called a "derecho" (hence the name).
I designed the map with strong hold areas, strong flanks, and an emphasis on height variation and open arenas. It also has a spire on second. Additionally, the shortest walk to mid is very quick and simple to do, but becomes a less useful route to use once the initial rollouts are passed (therefore balancing out the quick routes and making the other options more viable).
scout - 9:43 (17 seconds to mid, counting initial 5 stationary seconds of the map)
pyro/engi/sniper/spy - 9:40 (20 secs)
heavy - 9:36 (24 secs)
medic - 9:42 (18 secs)
I haven't tested enough to see what the best rollouts are in the map, but there are some really cool jumps for soldiers on the map, due to all the height variation.