He continues to pester me by phone.

Or would it just make sense to factor in my 10% Cap/Repairs/Vacancy/Management for the total rent of the building (planning on renting it from myself) instead of treating it like 2 seperate condos.

Make a referral to a contractor you know, or volunteer to stuff envelopes or answer the phone.

If you do your own repairs, than it will probably just be a pain.

Remember that most things start to give you signs they are failing month or years before they actually "let go" so if you are often repairing a large expense item be wary and contribute more to your buffer.

In fact I have all of my properties in trusts which makes my residents a part owner in the property and they are required to take care of all the upkeep and repairs on the property.

Also, the repairs and vacancy that inevitably come with operating rentals mean a negative cash flow.Negative cash flow + low chance of appreciation = yikes.

However, I hope you budgeted in losing the existing tenant, repairs, and vacancy because any major increase of rent = this reaction.

So here are the numbers...House current value - $1 millionARV (every room needs updating) - $1.35-1.4 millionUpdate/Repair estimate retail finishes - $150KUpdate/repair estimate rental grade finishes - $30KThey both don't have money to update the home to sell for top dollar, so they are willing to take the $1 million and move on. 

Some are good with monthly phone calls, but not more frequent.