Pressure washing is fine and pretty much a standard, but only to wash off the surface dirt. You just want the house clean, not stripped. Generally speaking, I would never paint cedar siding if it is the rough sewn style. If it is smooth wood, the paint is probably okay, but just remember that paint tends to peel and stain is more resistant to peeling. I'm sure this also depends on what was used before. As for the spraying, when painting wood it is usually preferable to actually brush or roll the paint on so that the paint penetrates properly. If you spray, it just sits on top of the wood. Some painters may actually spray the paint on the wood and then back brush it or back roll it which is essentially just using the sprayer to get the paint on quicker than you would be able to by brushing or rolling from a can or bucket. Then of course, there are the hacker idiot painters out there that spray everything regardless of the situation because it's just faster...these are usually the same guys that will get overspray all over your car and your grill sitting on the deck too so you need to be careful about who you hire. Honestly, anyone who would really spray the underside of your shingles because he is too lazy to prep the roofline properly would have me worried. If you decide to do it yourself, the method I would recommend is rolling the paint on. You can decide then if you like the look of the stipple or if you would prefer the brushed look. You can use the roller to just get the paint on fast and then brush it out...saves you a ton of dipping of the brush doing it this way. Only do a couple boards at a time and don't paint in the direct sun and try to keep a wet edge so that the paint does not dry too much as you move the ladder. Of course, if your siding is the rough sewn style of cedar, you can pretty much roll it and leave it as you will never be able to see if there is stipple or not when the wood is rough. Good luck!

Paintguy, thanks a lot for your thorough reply and recommendations. Our thoughts are in synch--maybe because I've read some of your posts before!

My siding--I'm not familiar enough with siding to know whether it is "rough-sewn" or "smooth"--was previously painted and I haven't noticed any peeling, just fading on the southern exposure. Its texture approximates what I've seen reproduced on Hardi-Plank, so I would say its rough and texturey, but certainly not bears-hanging-around-the-cabin-in-the-woods texture.

Rollers and brushes it'll be--thanks.