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Condo Purchase - Tax Strategies [US]
You will need to see a tax expert. Your edited question includes the line For the short term, we will be "renting" it to my wife's grandmother at a deep discount. According to the instructions for schedule E If you rented out a dwelling unit that you also used for personal   purposes during the year, you may not be able to deduct all the   expenses for the rental part. “Dwelling unit” (unit) means a house,   apartment, condominium, or similar property. For each property listed on line 1a, report the number of days in the   year each property was rented at fair rental value and the number of   days of personal use. A day of personal use is any day, or part of a day, that the unit was   used by: I have no idea how this will work for Schedule C.