If it was me? DIY. Otherwise, I’d probably take a heloc on the property and pay for the new exterior work with that.
Make sure you have a good wrb layer on your sheathing, consider r-10 of exterior insulation, then a rain screen, and then your siding. I would have no issues going back with vinyl, though. If property installed, it should have no problems lasting. We’ve got maybe 10 houses vinyl sided and very rarely have issues. You can also avoid a rain screen with vinyl, the siding “hangs” and allows for plenty of air flow.
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