My father seriously suggested painting one side a year. I don't think he realized that it's a small house and that we're going to paint it a different color (green). Once all the prep is done, we can easily get it painted in a day. -- If everything seems to be going well, you've obviously overlooked something.
My house is brick on the bottom half which will mean a lot of taping, drop cloths etc. The more I think about the more I think about just letting it go this year and setting aside money over the winter to just hire someone.