However, my contractor just happens to own a 3 or 4 unit on the next block and he said he's managed to keep students in his rental rotation fairly easily. 

If you don't want to go through 5 different contractors a good PM can probably give you a written opinion on the upgrades needed.This should help your family members understand what a fair number looks like, so nobody feels taken advantage off.

If they are VERY professional, they will have their processes in writing as verification that it is enforced equally and fairly by their entire staff. 6.

There are a lot of multi family properties in Charles village but they will fairly expensive and probably cash flow poorly by my standards.

There are lots of different types of "dementia"...it sounds like they are moving toward the adjudication process of formal guardianship, which is likely the right thing to do.In the interim, you can explore different types of guardianship, like "ad litem"...just consult with an attorney and I'm sure you guys can figure something out fairly quickly. 

This will give you a much better sense if the pice is one you feel is ‘fair’.  

You have to prove you are legit to them (which I think is fair). 

You get to take full advantage of the tax benefits and it is fairly passive.

If his spouse qualifies as a real estate professional, they could purchase the commercial property the business is located at and rent it to the existing business at a fair rental rate. 

I currently work as an appraiser, so I have a fairly intimate knowledge of the area and will help in any way I can.