HardDrive coincidentally that was our summer project last summer!
We rented a bucket truck though, something like this:
It was great! I was able to drive across our field to get to the back of our house with no problems negotiating rough terrain. The total extended length of the boom was about 45' if I recall and even when fully extended it was fairly stable. It took about 1/2 hour to learn the controls...a little tricky at first but you soon get the hang of it. It cost me $700.00 for 5 days.
We applied an elastomeric stucco "paint" to our two storey home:
All-in-all it took us about 2 weeks...the biggest PITA was taping though....that was not fun!
I bought a pre-owned industrial airless sprayer for $1000 off of kijiji.ca which made the job fairly straightforward. The total cost to me was about $4000.00.....before I undertook the project I got several quotes, all in the $15,000.00 range! Now my neighbour wants me to put in a bid on his place

.....I'll have to think about that for awhile!
As others have pointed out, if you do decide to take this project on, make sure to use a safety harness when you're up there. Ask me how I know?...I was spraying the top of one of the chimney stacks when suddenly a huge gust of wind hit me and almost catapulted me out the bucket at 35'...close call!
Cheers!
Alex