Once you have cash in hand, you can unlock the unit for 24 hours and let him move his stuff out.I would also consider charging an additional deposit of $500 or something, just to prevent him from leaving all the trash or stealing your refrigerator.

These are professionals with additional training and a stricter code of ethics.

Be prepared to come in with additional cash to close due the the appraisal.   

@Patrick Braswell Got it. just didn't want you to spend all the time working with your family members if the bank won't approve a HEL.

You indeed have to spend that much money.

@Luis Cerwin as others have stated, Nov - Jan is the worst time of year to have a vacancy.Majority of tenants live paycheck-to-paycheck, so all their income goes to Holiday spending starting with Halloween, then Thanksgiving, then xmas, then NYE.January is also historically the worst month for rent payments due to Holiday Hangover Spending.

Every time I change cleaners, I spend at least 3-5 hours retraining on my processes and expectations and even then things are missed.

I'll just add that in addition to offsetting future tax liability, I'd like to offset current taxes as well, during my highest earning years. 

Also, be sure to have your LLC as an "additional insured" on their insurance policy as well.

Sounds like you put in a ton of work to maximize the value, and that basement addition was a smart move.I noticed you mentioned the NYC luxury tax and some of the rental pricing challenges—have you considered expanding your portfolio in markets where you don’t have to deal with those kinds of headaches?