Our lumberyard sells the Sierra Primed Shake Deep Groove in 20 board bundles at $168.30 per bundle, which breaks down to approx $8.40 per 8' board. We did price out the pre-finished in Maple too...$259.25 per bundle or approx $12.96 per board. Those prices are with a 15% discount that they very kindly offered since we're OBing. :o)

If the substrate is in poor condition you may have an adhesion problem. That doesn't mean it won't adhere today, but it does mean it may peel in a few weeks or a few months. It all depends on the moisture content inside the failing shingle. Given that the siding is failing, I wouldn't prime it. I would repaint it with a solid color acrylic stain. Even so, that product requires prepping steps to achieve proper adhesion. Sherwin Williams Woodscapes is one product.

Chris your inspiration house has a large proportion of the natural cedar color to the blue and a lot of what we can see on that house in the photo is in shadow which makes a big difference. You're trying to choose a color for your house without a clean background - the yellow is a player in making colors look different. I took a picture of 2 colors from one of my paint decks for you - put them on a table on our porch that is similar in color to your cedar but when I compare the picture to the paint deck it's horribly off so I hesitate to post it for you. I may email it but just know that it's not representational at all. I'm looking at Benjamin Moore Everard Blue CW-575 and Wetherburn's Blue CW-580. these are from their Williamsburg collection, grayed blues with green in them. Even on the B/M website the colors are off on my computer. I'm not certain these are the *right* colors for your house but it's a slightly different direction that brings your setting into the mix and a place to start. Hale Navy is part of the Historical Color collection from B/M - that collection is a good place to be as well. The colors are dirtier which is good - what you don't want is a bright, clear color on your house. There are different ways to approach trim and house colors - they can be high contrast with crisp definition or lower contrast and more subtle transition. Neither one is better, they are just different looks but your trim will still be differentiated from the house body with less contrast. Are you planning to paint your eves and rake boards like the inspiration house?

Sympathy extended. I suspect it doesn't look as bad to anyone else as it does to you. Before going "whole hog" on trying to strip that paint off, consider all the advise you get, then experiment on a tile or two located where it will be least obvious if it doesn't work. Do you still have some of the paint you used? If you have any shakes left over from when they were put on the house (yeah, long shot), paint one and then try stripping the paint back off. Because of the thin/side edges, removing that paint by hand will be a real chore. I suspect sandblasting has the potential to damage the shakes. You'd likely come out better adding to -- covering -- rather than trying to remove -- that paint. If you're thinking about replacing the siding and if you like a rustic look … but don't want to go through this again … something to consider: https://www.loghomeshoppe.com/pine-quarter-log-siding.html Good luck.