pete, I would rent the pressure wahser as a good unit (10hp or more) runs over a grand. Go slow and with the right tip all the loose paint will come off. (A 0 deg tip will actually cut through the wood!) I would buy the sprayer because you can get a decent one for under $300 and the rental is about 50 a day. You would need to rent it at least two times so you would have already paid a third of what it costs to buy one and you can do it at your leisure. Rent one and I guarantee the day you set aside to paint it will rain /w3tcompact/icons/sad.gif. I think an oil primer with a latex topcoat is what is recommended, check with the paint store. If you use a ladder that's what will take the most time, going up and down and moving the ladder. 40 foot and you will need a pretty good extension ladder. Takes a little getting used to but you'll be amazed at how quick it goes. (Most put on about .40 gal per minute at full output) You can adjust the output, you dial it down for primer and stain, dial it up for paint and thicker stuff. Trick is to keep the spray patter at 90 deg to the surface and have the tip moving before depressing trigger AND after letting up. Get a more even coat and avoids globbing. Ideally you can have someone follow you with a long brush and backbrush or you can do it yourself. (Spray section, grab a wide brush that you use to wash cars and run it up and down a few times. Works the pain in and evens things out nicely. I used one of those extension poles that extend out to about 15 feet so most of the back brushing is done from the ground). OH BYTW - airless compressors are self contained, don't need a compressor, they operate like a pressure washer at about 1500psi. When shopping do yourself a favor and get the 50 foot hose. Most of the cheaper ones come with 25 foot. It's worth the extra money to get the 50 foot hose, saves a lot of time and moving things around and you'll be able to do your 40 foot peaks. Not a real hard do it yourself project, you can save a ton of money, and if you do it right you won't have to do it again for several years. (Just make sure you run either thinner or water through the hoses when done to clear the pain left in the hose and pump)