My House WAS 2 summer guest cottages,
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do your self a favor and remove the existing finish ,chances are it may have been a quick fix
what kind of siding do you want?
When we removed the siding from our 100+ year house we confirmed it was a plank house with no sheathing. We put outdoor grade plywood on it, a Tyvek barrier and then put the siding on. We started running over budget, so just did the North side of our house that way, insulating with foam sheets on the rest before putting on siding. The north side of our house is the quietest side of the house and the warmest, even though it gets wind all winter and is by a busy street. Years later, I wish we had done the entire house that way. You get what you pay for, and it wasn't really that much more to do the extra step. The sheathing was 4x8 sheets and our house is fairly large but that step only took a day.
Wow! What a great project! I would check your local building codes before proceeding. You also want to make sure it is properly insulated too.
Good luck with this project!