I'm just getting into the investing game myself, looking to add income stream to supplement a law practice and real estate brokerage.  

This property if held will have negative cash flow requiring you to supplement your tenants rent monthly due to long term expenses.

Just curious if anyone uses Truthfinder to do additional “screening” or background verification for tenants? I’ve used it to avoid a bad potential business partnership, I even showed it to him and he literally had his...

Suggest you go the electric route--less or  no maintenance costs, and when repair is needed, inexpensive compared to most gas fired boilers or furnaces.I would also have a small natural gas wall space heater installed somewhere on the main living floor (not in bedrooms) just in case of power outage and / or for supplemental heating.  

Wouldn’t supplemental insurance cover anything else that Airbnb’s insurance doesn’t cover?

Are you looking to create financial freedom on investing, or is this just a supplement to a holistic retirement strategy?

During 2009 when I bought my condo in SF, to supplement my vacation income, I signed up with a company called Air BnB to rent out my place when I was gone.  

I supplement the costs of all these repairs with my day-job salary, otherwise this would all be over a long time ago.

My goals aren't fully defined yet (working on that soon) but in the short term I hope to bring in enough passive income in the next 3-4 years that we can supplement my wife's salary giving her more freedom and flexibility as we look to start a family. 

Also....if you already own a property literally within 100 miles of where you are trying to get the FHA loan then the FHA will not let you get that loan.Other then that it is VERY similar to the VA Loan.If you're getting orders to another base....I would simply wait until you get there and (as long as it's 100 miles away from where your VA loan is) then use the FHA loan to buy a small multifamily.Live there for a year in the FHA property.....THEN refi out of your FIRST VA loan........turn it into a conventional loan.......and then Get a VA Loan at the new duty station that you got the FHA loan at.....then when you get orders somewhere else....REPEAT.I know of people that did this VERY succesfully when I was in the Navy and when they did their 20 years they ended up with 2 properties at each duty station every 3 or 4 years for a total of 20 plus duplexes that supplemented their military pension and literally were able to retire at 39 and 40 years old respectively.