The main reason I care is I don't want to have to spend $1000 or more every year on the tax prep when all I probably need to do is file on the Schedule E (especially with just one or two properties). 

Built in early 1900s but have had all updates and well taken care of. 

Someone has to take care of our seniors so its good that you will do so.

Built in early 1900s but have had all updates and well taken care of. 

You need to be careful.

Do appraisers price in these circumstances or do they only care about the selling price, square footage, lot size, and number of units?  

I would be careful entering into an agreement like this with someone I didn't know. 

I always look at it from the perspective I don’t care what there number is, what is my number ?

There are those who purchase in their own name, then transfer to an LLC, not caring about the due-on-sale clause issue. 

Now Landlords are care givers...but Im sure you ran your comps.