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Permitting the garage conversion will likely update the square footage on the tax rolls (and increase your tax bill accordingly).

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That's typically more expensive and less favorable borrower terms, so it turns off a lot of buyers.Depending on the part of town that it's in, a good exit strategy could be to do a condo conversion and sell of each unit individually.

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Besides day-to-day stuff (lease ups, paperwork, maint), you should be able to have a regular conversation (monthly?)

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Is that about how that conversation goes?

I do think it's worth having a deeper conversation with your tax professional.