It has been a while since I posted this, but the box is up. Few small changes in the hardware specs now. It is an Intel Xeon Quad Core processor, 2gb ram (most servers run fine on 1gb, it is the least of worries with SRCDS) and so on. A very badass server indeed.
Problem I ran into is this. I am hosting 24 slot Pub, 32 slot pub, 2 16 slot match servers, and 1 testing server for the TF2 mod I am making. I will just need to buy another IP address (it came with 5) from the company for this and I should be good to go.
1) Yes, it will always be running. This is a dedicated server that is setup to do nothing except run my TF2 servers.
2) I am working on it now, but biggest problem is just going to be getting an FTP setup for you guys to upload your files to. Currently the only FTP I have setup is for me to manage the gameservers, so I would need to get that worked out (securly)
The only other option I am considering, is possibly doing like a schedule. You guys send me your maps you want hosted, and I will put them up on a server for you at a select time (within 12-24 hours about)