Indy, coming to NM from Colorado or TX is like saying, "hey, while I am in Bangor I will just drop by and visit you in philadelphia." I appreciate the offer and would be happy to buy you a steak sometime but don't come here just to install my new OS. I am sure I can find someone else local. You guys make it sound like he/she doesn't need to be a genius to pull it off.... not that you are not geniuses.
Bill, given what you want the server to do, and your desire to self-manage, I would drop in the new drives (RAIDed), perhaps a SSD for the AC folder if you "feel the need for speed", and install Windows 7 Ultimate.
Some will scream "sacrilege!", but the less moving parts, the better, and I'm going to side with JBS on this one, give the man his P2P.
As to traveling, I purposely drive sometimes to decompress, so a few hundred miles could literally be just a few more conference calls than normal.
There was a particularly stressful corporate engagement a few years ago that required weekly travel between locations; I put over 12,000 miles on a rental car in a month.
So, I'm serious about swinging through NM to help a Doc.