Is there a possibility of running Orange with multiple maps on a map rotation similar to other non-24/7 map skial servers or is it the current one the only one that will fill?
What exactly do you have in mind? I don't see much value in changing orange maps. Most people leave when the map changes and oranges maps are quite similar, x3 is the most popular.
Does skial have a gravelpit? I have not played that map since I started tf2 years ago.