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just trying to get a feel for where the line is drawn.

As usual, if you want clarity you need to seek it outside of tax law. The only easy part is that, for personal-use property, repairs/maintenance have no tax effect and improvements add to the basis.

OP asked about painting the house. To me that's routine maintenance, IOW, it holds the status quo. New vinyl siding (secrets of the Universe and steak knives optional) would be an improvement, at least from a tax perspective. Patching a roof is repair; roof replacement is an improvement.

You mentioned rehabbing. That is an improvement even if individual items in it would be routine maintenance. However, should you take 20 years to do a rehab, as did a friend of mine, subsequent painting, carpeting, etc. would be maintenance.

There's some, but not much, help in IRS Pubs 527 and 551. (Pub 527 is for rental property, but the improvement/repair discussion is valid for all.) My advice to OP would be to keep records of everything and at the time it would matter (when the property is sold or converted to a rental), seek professional advice if there are significant issues.

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