cedar siding painting/staining questions

Hello all, I have a 25 year house with rough sawn cedar plank siding, layed horizontally and diagonally. BTW,this is in the Seattle area. It has a previous brown oil based exterior stain. Currently it is beginning to look its age. There are some areas of mold/mildew
Here is what I have gleaned from reading this forum:
Cleaning the cedar siding: =================( Bad) Bleach,TSP, Pressure washing, sanding (because its rough sawn cedar) ( Good) Washing with oxyclean
So I am planning of washing it with a sprayer, I thnk it says 150 psi on the box. So how high a pressue is too high for cedar siding ?
What kind of wash do I use on the house ? I also have a deck brush from home depot which connects to the hose. Can I use one of those on it ? The house is pretty dirty and hasnt been cared for very much by the previous owners.
Caulk: ===there are some holes in the siding which our friendly neighborhood woodpeckers have made, can I fill these in with caulk. Which comes first washing the siding or caulking all the holes ? If its caulking first, how long do I need to wait before I wash the siding ?
Paint or stain : =========My husband wants a paint since it really DOES look nice, I have read paint is a PITA to maintain, ie, needs to be scraped off etc., before repainting, whereas stain degrades. I am leaning towards an acrylic-based stain. I have the color i want, and when we tested with a Kelly Moore paint. Does anyone have any ideas how their stains hold up ? If there is someone out there from the Seattle area who has suggestions about what works best for the local weather...
Painting technique: ============I bough a wagner paint crew and it sprays nicely. But I want to make sure I dont put a super THICK layer of paint which loses its elasticity. Do you have any tips on how I should do the painting and recoating? Do I paint the entire house followed by asecond coat in a couple of weeks or recoat the same day in a few hours ?
Safety: ====Its a split level with a rather tall roof. The house is on a sloped lot, so I am a little concerned about the stability of the ladder. We have a 24 foot ladder, and I am very nervous about letting my husband go up on it. Is there anything I can do to make it super-stable ? Dont laugh, what about tying oneself to the roof with something ? What about scaffolding ? do people rent them out, is it hard to assemble ?
Any other words of wisdom or cautionary tales about painting, you can throw my way I'd really appreciate it.
Thanks A
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