HO insurance that doesn't know about short term activities will likely deny claims.

I suspect your realtor is going to have a hard time rebutting the appraisal and will fail if he tries to rebut it either on income or claiming the "studio" is a 3rd unit.Good luck

This ensures that any liability claims that arise while the property is under management are undeniably covered by your policy.

Claiming it as being used 50% v. 75% is a $25 decision.

The one place they have rented (an apartment/townhome) they claim they broke the lease and moved due to a mold problem that they couldn't get management to rectify.

On the other hand, you can claim depreciation, which is tax deductible but not actually paid out of pocket. 

A Small Claims Judge will laugh him out of court.

(I believe it is 15 days to return the deposit if there's no claim and 30 days to give a written notice if there is a claim)I would think that she is responsible though since she never notified you about him moving in.I'd confirm that with an attorney though just to be safe.

Your Agent should be able to help you with how the claim will be processed, why the payout is less than you expect, etc...

Given that there will be no exchange of cash or any other considerations, I believe I will need a quit claim deed to transfer the property (feel free to correct me if I am wrong).