Here is the situation, I have a colleague who owns a handful of rentals and is looking to get out of handling them and retiring. 

Hi,I am wondering if someone would be able to assist me in a good streamline process for handling utility bills.

But like @Mike M. said, if you have a seller who is truly incapable of making decisions for himself, you'll need physicians to certify this in a petition for guardianship plus you'll need a fiduciary appointed to handle those decisions for him... in his best interest. 

I would contact an attorney that specializes in evictions or find a and handle this legally and properly.

This is a point at which your tenants will probably either gain or lose a lot of respect for you depending on how it's handled.

I'm located in NYC, but due to the gentrification happening the market entry is too high for me right now.

My husband and I are wanting to get a multi-family and are thinking a great way to get my brother involved is the following: My brother would get an FHA loan for a triplex or 4-plex in FloridaI would put the 3.5% down payment as a co-borrowerMy brother and his fiancé would live in one of the units for a few years rent free so they can save money for a houseMy brother would manage the property by showing units, cleaning them when someone moves out, and as much maintenance as he can handle on his ownI would handle the finances paying the mortgage using the cash flow and keep the profits since my brother is living rent freeMy brother would move out eventually (2 or 3 years later) and we would refinance into a regular mortgage so that he can get another FHA loanWe would begin splitting all profits 50/50 once he moves outMy question is, has anyone reading this done this before?

Given that I live in the bay area, I know that barrier to entry is pretty steep here, so I'm looking in neighboring cities like Sacramento, Stockton and so on.

The barrier to entry for a first time home buyer owner occupant is incredibly low and efficient with the number of low down payment loan options and excellent interest rates and terms.

Need some advice on how to handle a tricky situation.