If this is Hardie, we know that that product is well above our budget. Do you know of a similar vinyl product and color?

"I certainly can... I was hoping that the community in total would be more knowledgeable than an employee at the lumber yard :)" Do you have an end picture? How is it uput to together? It looks like it may be a Pattern 105 / Log Cabin - possible custom run but no way of knowing for sure without an end shot. But I would take it to a local lumberyard as Charles states. Unless it was immensley popular regionally it will be tough to match anywhere however.

I must say, the aged look of the shingles is quite beautiful to me. Sounds like (from the above) that doing your spot repairs as needed could be the way to go, both esthetically and financially. May I ask pros for more detail about how you would prep either for clear finish or paint if thats the route someone wanted to go? If wood is dark do you assume that its mildew (prob use deck clearner type product?) or is it just some natural aging (patina) of the wood that could take a clear finish over it? Just curious - dont have a shingle house at the moment but almost did once. If the damage is limited conceivably OP could use an epoxy-base d wood hardener + wood fill product on it? Generally my experience with 100 yr old wood is :-) and not :-( This is likely still old growth timber and as such was hard as nails very unlike the farmed wood of today (and still is, if its not too rotted) Was so shocked when I got some cedar trim milled for my old porch at how soft and splintery it was - nothing like the existing wood. And I would reiterate about trying to find someone local who is old house friendly and has wood restoration in his/her repertoire - either to do the actual work or you pay them for a consultation. Your plastic guys - siding, windows, etc. - have their own business model and ways of doing things so you really cant expect them to be knowledgeable in other methods. Its fine with me if thats what they want to do, but where I have a problem is when they dont recognize their limitations and make these pronouncements about how the old siding or windows have to go .... like its some kind of ulitimate truth. Consequently, a lot of people dont look any further and the end result is ... at least in my neck of the woods.... a lot of plastic-clad houses.

Sometimes it is not the material, but how it is applied. Installing cypress with J-channel at every termination will make it look like vinyl siding. The first step would be to make sure you have a "farmhouse" design in form, proportion, and fenestration.