I bought a JLG T350 towable boom-lift trailer just for this purpose. You can also rent these by the day, weekend or week. I rented a Nifty-Lift and a JLG before buying mine (former builder, 1/2 price, needed some stuff fixed). Mine has electric, air and power-washing connections at the base that run up to the bucket, so I can hook into these lines from topside. I feel this is the only safe way to operate at the higher elevations. Falling off a ladder or a plank between ladders will never have a good outcome. With a centrally located parking point, you can go to within inches of areas that need attention. The only warning is when working around power lines. After that, a Power Painter (or whatever) that can suck from a can makes the job go really fast. Having an accomplice on the ground to keep the bucket in a favorable position is really cool. Having two hands free to hold tools, painters, beverages, etc. adds another degree of safety and confidence.
While you are at it, trim the trees, check the gutters and the chimney. Mine goes up abut 35 feet to the base of the bucket. Once you get used to the situation you loose the natural fear of flying. Looking down is OK. Looking UP at moving clouds is not recommended.
When you are done, you can easily sell it for what you paid (or more). Beware of a long line of neighbors and friends wanting to borrow it.