First off get up at 6AM. (its going be a work day) find their number. Call them. ANd by 5PM if your lucky you'll be done. LOL JK. When my dad installed XP on my comp we had it done in about 45 mins.
50 times a month is a little overkill. I phone in like two or three times a year so they have good reason to believe that it may be a system failure that have to result in a complete restore.
Erm this year we've prob done it 8 or so times. IDK about you but I don't feel the need to buy a 250$ piece of software for EVERY SINGLE COMPUTER (we got 3) thats 750$ and if microsoft honsetly thinks they can get that then they crazy. Also you gotta remember. I bet most microsoft employees really don't care as long as they get their paycheck. So ya should be fine.