Our CPA said they would have to depreciate the amount invested over the life of the property... so it would be only about 5%.

The insurance estimates I got was $900 annual premium for each duplex (at $140K replaceing cost).

But I also know these are people who need a work/life balance.

Glad you are preparing for life after the NFL, as so many athletes do not do so.

If you want to market the certificate, then you market it as a tax certificate and see if anyone wants to buy it.If you got a deed then you need to know if it's insurable or not.

Not to mention upkeep (repairs, taxes, water, insurance) of her personal property (reverse mortgage) and mine.

Creating an LLC from the get go and purchasing properties through it would exclude you from utilizing this financing.I run a $40 Million portfolio in the Cleveland area & I can tell you even at that scale the risk of a life changing lawsuit is incredibly low, especially if you are acting like a responsible property owner.

If a seller is on board with a short sale, usually their credit is not perfectly sterling anyway..if they cannot afford the house any longer and may end up losing it anyway, I believe that It is better to get them some funds to move on with their life from the bank and also to make a profit for myself or a client.  

I also know great people for home insurance policies, a great loan officer etc.  

Currently renting out the old primary residence at $1800/month with a cashflow (after mortgage, insurance, taxes, vacancy, maintenance, cap ex, etc.) of over $500/month; with the other two investments each pulling in between $250-350 a month.I also decided to make tennis my "full-time" job and pursue real estate more heavily as my career.