While I can imagine some cities might be against "boarding houses" or enforce their "brothel law" I can't imagine too many cities would be supportive of it. 

From updated tenant rights laws to shifting zoning regulations, staying compliant can feel like a moving target.

I think you need to find a good local agent, network with investors(local meet ups, FB groups, etc) and learn more to dial in the gameplan. 

It seems you and your husband have the ability to make a property more desirable and I would try to stay local for the same reasons you listed. 

The property was listed in the MLS by a local agent who was also the owner.

I'm not even going to show it to them.Just be careful that your prescreening questions/discussions follow Fair Housing law and are asked of everyone. 

Hi, I’m Drew, the owner of your local PMI franchise, PMI Two Rivers, here in Nashville.

Quote from @Lee Banks: Hi my name is Lee I'm looking too buy my first rental property and but I feel as if I need a mentor to watch, I still need to learn the basics of real-estate does anyone in New York do programs or mentorships and where would you start if you first started real-estate today  Hello Lee,I'd recommend looking up local meetups here on BP, meetup.com and, eventbrite.You can also call around to speak with RE investors and professionals in your target market to begin making connections.With so much available information online, I'd recommend speaking to a few people and doing independent research before committing to mentorships.

ROI can vary, but some parking lots have great returns with minimal upkeep—just be sure to research zoning laws, demand, and operational costs before diving in.Good luck with your decision, and feel free to reach out if you want to chat more about any of these options! 

Keeping your STR local would be the best case.