Siding Update with insulation Install - But No Sheathing

Siding Update with insulation Install - But No Sheathing #green

New here, but have been trying to suck up the knowledge as best as possible. Im sure this is the first of several questions, so forgive me if Im not providing enough/the right info to get things started. I own an old farmhouse, right on the 5A/6A climate border. Its a foursquare type, with a few additions tacked on the back of it. My questions focus on the main part of the house, since its mostly original everywhere. Build date is circa 1880, built with a mix of new/reclaimed timbers (based on beams in the basement). There is currently wood clap siding that is in pretty poor shape (needs paint, many are cupped/warped/split, brittle when trying to nail them). So, I dont like the siding currently, but the rest of the original details are there and in great shape. I want to keep all those. First choice is to use fiber cement as a replacement, and there is the distant thought ...

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