Hi @Harry Maxtens, I'm not sure where you are located but you may want to start by looking into the local regulations for property management/managers.

Good renters may not be easy to come by. sometimes as cashflow is the best interest, but a good screening and understanding of house rules and regulations should be discussed in detail.

Hey BP, I'm curious what issues you're most concerned about when it comes to passing an IRS audit and staying compliant with all regulations we have to follow? 

I was told by a lender that due to regulations with Fannie Mae and Freddie Mac, I cannot refinance on a property with a cash out until I’ve owned the property 6 months.

The narrative tying that together was complete rubbish, something about how a polsci major understands gov'ts, and mortgages are regulated by gov'ts, it was a joke.... but it got me into a house.Might be advantageous to find an independent mortgage broker local to where you are buying that works with multiple lenders.

CA just passed a Statewide Rent Control ordinance as part of their renter protection plan, Minneapolis is working on similar regulations.

Spend an hour with your CPA so you setup a tax procedure and to maximize your tax savings.

Just know the regulations in the area before you buy. 

If one mortgage foreclosed, and the other mortgage was not involved in the proceedings, the surplus goes back to the homeowner.I got in a heated discussion last week with the paralegal of a large law firm that handles a lot of foreclosures in my area and I was not happy with what she described as "normal" procedures for her office.

@Wendy FateIf you do decide to dive into assisted living, then keep in mind it's really two things in one: buying (or renting real estate) and operating a regulated business.