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Default 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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