If changing over to a new exterior material then consider manufactured stone:
http://www.coronado.com/redesign/product_index.html
If you have a compressor then you could buy a pressure paint tank and spray your house. I bought one at Sears years ago and did a friend's entire townhouse interior, then used it on my homes interior 8 years ago. I don't see why it wouldn't work great on the outside. BTW, I used an old 1 HP/13 gallon Sears compressor which worked perfectly. That and 50 feet (x2) of light weight air and paint hose, and an old (Sears/Devilbiss) spray gun head and you're in business. You can even place a gallon paint can in some models and avoid most of the mess.
Also, consider the possible legalities when removing the old paint. If lead is present MA may require a certified individual/organization to remove....kind of like with asbestos.
HF 2 1/2 gallon pressure paint tank(only) @ $39:
http://www.harborfreight.com/cpi/ctaf/Displayitem.taf?itemnumber=37515
Here's a used Binks for $100
http://cgi.ebay.com/ws/eBayISAPI.dll?ViewItem&category=26228&item=7518503023&rd=1&ssPageName=WDVW
Ebay listings:
http://search.ebay.com/pressure-paint-tank_W0QQfkrZ1QQfromZR8
EBAY Entire pressure paint setup now @ $51 pressure paint tank
