I have a question that i've been concerned about for a while now.
I know right now that I will probably be switching servers quite often as I make more money and upgrade so my question is, is it possible to take all the files/databases from one server and move them to your new server with all your shared/reseller hosting accounts still the same? If so, how hard is this process and how long does it take?
It's much easier with a control panel such as cPanel. WHM itself has a transfer feature that makes moving accounts very easy. Your best bet would be to hire an experienced server administrator to handle this for you.