Janus,
Several months ago I decided I was going to paint my own house. Figured it couldn't be THAT difficult. I mean, I've seen the commercials for the Wagner Power Painters and the like....they have the whole neighborhood painted in a matter of seconds!!!
Picked up some prep supplies from the local Home Depot. Wire brushes, sandpaper, bondo for replacing any rotten wood, etc, etc, etc...
It was a Saturday morning, around 10ish, I believe. Started out, wirebrushing peeling paint, sanding it smooth....30 minutes of this and I had enough. by 11:00 I had all my stuff cleaned up and was in the house calling local painters to schedule some appointments for quotes.
By the next weekend, I had found the painters I wanted to use. They were scheduled, and two weeks later, my house was finished. It looked marvelous!!!! Even my neighbors tought so!
Personally, I'd contract it out.
Here's a couple shots of the back of my house. The other three sides are brick....not a lot of paint there, except for the trim and soffets.
Have fun!!!!
Randy