Allowing the elderly owner of the third house to continue to live in and only pay me a break even (taxes, insurance, maintenance) rent amount.

In that sale, the sellers were elderly, sick, uncollectible, and a hefty upfront payment in exchange for a sub 2 would have actually benefited them more than an outright sale (long story).

I have many times seen title company balk though and worry about elder abuse etc. and they will want the seller to come in in person and sometimes they will want letter from Sellers attorney saying they agree with the transaction as written etc. 

2 does he have income3 does he have assets4 if you do this without him getting legal advice, you may have a problem in the future.5 look up the elder abuse laws in ca.

@Sam Elder - Hey!

More in the "do the dumbest things" category....We get a frantic 11:30 pm call from an elderly tenant crying incoherently but after several minutes my wife determined it was because water was 'pouring' in the bedroom window.My wife distinctly asked her several times if our maintenance guy was called & if he was there as he was not answering his cell. 

Second, I would want you to explain to me that she is elderly and disabled and would just prefer to handle the business transaction all at once (if that is what I read correctly here).

Maybe installing a grab bar in a shower for an elderly tenant who needs it to safely enter/exit the shower.

I think the real crime here is that families no longer take care of their elderly.

@David Rutledge I don't doubt it, but it's a town of about 20,000 people, and aside from this thing a number of miles away called the Pro Football Hall of Fame, there really isn't anything that spectacular to draw tourism in the area... it must all be corporate and maybe kids returning to visit their elderly parents?