Paint and maybe refinish shingles on exterior of our house?

We live in a Craftsman-ish house in Berkeley, built in 1908. The previous owners went the cheap route and painted (AAAAGH!) the redwood shingles on the second floor exterior of the house, as well as the wooden siding on the exterior first floor. The house is two stories, 2,000 square feet, very tall, and needs repainting. The original window frames and sills and a lot of the house should be sanded first, or something like that, as the paint is peeling in some spots. Rather than repainting the entire house, I would like to have the paint removed from the shingles and have them stained/refinished, but I am afraid that this will cost an arm and a leg. What have you paid recently to have a good deal of prep work done and a similar sized house painted? Have you had paint removed from shingles and the shingles refinished, and if so, what did that cost? Finally, can you give me some local recommendations to do the work? Any other suggestions or things I should consider? Thank you for your help!

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We have a similar 1907 Craftsman house with shingles.  (Shingles are cedar, not redwood.)  It would be quite costly to remove the paint for the shingles and they won't be able to remove all of the paint so it's not good.  Have you thought about re-shingling the entire house?  It will great.  The problem with doing anything with wood right now are the prices.  Wood prices are doubled if not tripled over the past year.  Over the years we have tried to sand and stain the windows in the front of our house.  The wood is so far gone it only looks good for a couple of years/.  We finally decided to get a quote....  $18,000 just to replace the windows or $25k to repair the existing windows.

With all of the fires you are going to have a difficult time finding someone to do this type of work.

It’s not feasible to remove paint from shingles. You can simply reshingle. I recommend this if the shingles are old since often people paint shingles when they are badly deteriorated in order to hide the damage.

When reshingling you can either leave them to weather naturally, or apply stain. If you plan to stain, have your contractor stain them by dipping BEFORE putting them up. The stain will penetrate on all sides and be much more durable.