Yes $4.99/mo is pretty reasonable. I also agree with you about the "real time" nature of on the air QSOs. Yes, an hour is plenty... I enjoy the convenience and high signal to noise ratio of the server, very helpful when I'm still trying to build speed. It does work surprisingly well. Setup can be painful, and when it's running it's not ideal, but still has loads of value.
Thanks again for covering the cost, and I'll be glad to chip in when the time comes.
If you wouldn't mind, please point me to your time and frequency for your 20 meter operation -- I definitely want to listen in.