Hey all I need help trying to figure out what to do with my 100 year old rental property. Specifically the siding, soffits, facsia, and because it's 100 years old it has no insulation. When I purchased the property it had already declined under differed maintenance, and after fixing up the interior now I'm on the exterior and I have no idea what to do. Here is my goals with the exterior project. 1.Fix all damaged areas and get a reasonable seal for a 100 year old house. 2.Improve the curb appeal for future residents. 3.Preserve as much of the historic look of this property as possible. 4.Keep costs way down because it's a rental and ROI is king. That being said so far I've got 1 estimate for $15k for vinyl siding and 3/4 inch foam board, and that estimate didn't include soffits and fascia. I know the house is huge, but $15k to just slap vinyl over the current exterior seems ridiculous, and its really only goals 2 and 4 that it "kind of" accomplishes. I can do the work myself. I've done just about everything except siding with reasonable results for a DIYer. So would you tear off the old siding, insulate in the walls and then vinyl over the top? Do it in small sections to keep it reasonable? Am I over thinking it and just let somebody slap siding over the top? I've attached some pictures.