If we were to rent out the unit we live in the place would cashflow, even if it were slightly bellow market rent.  

Even in the Excess/Surplus lines it was difficult to find a company willing to write it.  

Even then some things don't always fit and you have to come up with a work around.Hire a separate landscaper to finish it all up for better curb appeal**all in all was very happy with outcome & quality** Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

I’m about 4 years from retirement and regretting not venturing into this world sooner.I’m currently going back and forth on whether to focus on short term rentals in Florida (Destin, PCB) or long-term single family homes in the Birmingham, Al area.

There are many mid-west states that are great for investing, even in today's market.

I would definitely be calling Airbnb on that for sure.I brought up a recent bad experience with some NFL players lighting off fireworks and setting the house and their car on fire and then blaming it on the neighbors even though we have a ring doorbell there (+ neighbors ring doorbells!).

It's not unusual to see 3/1 and 4/1 Section 8 properties but that single bathroom would not do well as an MTR.Overall, I'd say location and the shape of the property is going to be your key driver and the factors that will make or break you in the MTR space so very carefully evaluate both before you make your decision. 

Even though the time frame to monetize is longer.

Even retirees get raises to their Social Security and usually pensions as well. 

I am looking at establishing a new single-member LLC.