I have known of people who retire from the service and supplement their income using REI just fine and it works out for them very well...not to mention the favorable VA loans you would presumably be able to get as a veteran.Also, my best friend (and best man at my wedding) is a broker in Marengo...about 30 mins from Hoffman Estates.

It is essentially sharing a property with tenants whether that is a room, basement, adu, etc in which their rent supplements the mortgage.

To supplement the rental cash flow, I am very interested in wholesaling properties as well.

Them someone is going to get hit with a supplemental tax assessment for taxes at the new appraised value.

The section 8 people you want are the ones that work to supplement their government income.

If you want to be a real estate agent as well to supplement your income or for that to be your future career, get really good at that so you can earn a high income.

Going through a property with a clipboard that has rooms and you take notes as far as what is needed and then supplement it with photos allows you to go over the notes after a walk through and develop estimates or define what supplemental walk through / inspections are warranted. 

I imagine keeping the listing tightly posted on AirBnb and furnished finder, or working directly with someone at a local hospital that sources housing or offers recommendations to travelers would be the most productive marketing strategy.I agree, the MLS is meant to supplement the strategy, the key will be how much effort the owner puts into the avenues you mentioned.  

For the "local little person" who is having a difficult time keeping ahead of the rising costs of living, as well as an employment market that overall has mostly low paying jobs, operating STR's was a nice way to supplement their income - plus is also helped increased property values.  

Now, if he is getting another supplement through Medicaid or some other means-tested program, that may be a different story.