Don't trespass, but standing on the street or sidewalk and seeing how the house is put together is perfectly legal. 

There are a lot of great meetings and resources around here that are geared towards investors.

You have to stand out from the competition to do well since there are so many rentals there.

Property is located in Illinois.Here is where it stands as of now:- cash out refi about to be complete.

The issues I ran into was the local market was already flooded with STR's and in order to be profitable you had to stand out with a home that was either near an attraction (ie great view, Garden of the Gods, Downtown, or a College) or the unit had to have amenities (Hot tub, Instagram Wall, Pickle Ball Court) that would place your listing far and above other similar listings.I think you should strongly consider if you more interested in moving away and starting a life somewhere else, or in creating a cash flowing investment to supplement your income? 

Have an Agent look into Stand alone Umbrella carriers3.

Yes, I do agree that this niche is getting crowded now and we’d need to stand out to be looked at.

For a long standing good tenant I may even waive it.

It has no upside, and nothing remotely positive about it. even if there were some situations where it would benefit both parties (and it doesn't) it is still wrong on its face, the whole concept is against what we stand for.

@Gloria N Gear I’d be happy to reach out to discuss potential markets in Indiana.