I'm looking at a property that is in an HOA that does not allow short-term rentals but wondering if there's like structure I can utilize in order to buy the property and rent it. 

When you talk to his case worker, I'd suggest you ask them to visit him and do an assessment as you are worried about his mental health.

I'm not sure if you're house hacking, but commonly suggested marketing sites for long term rentals are zillow, apartments.com, and Facebook.If you're interested in doing short term rentals Airbnb, VRBO, Booking.com, and Furnished Finder.I hope this helps!

@Krishn JAISWAL welcome to the wonderful world of BP. 

Hi Sharon,If the yard is not separated, I would suggest hiring a lawn care company for weekly/bi-weekly service.

My suggestion is to go long with the vendor financing.

I'll definitely take your suggestions to heart, especially about exploring side gigs for extra cash, budgeting diligently, and leveraging resources like local real estate groups and mentorship.

(I'm curious about Louisville and wondering if I should avoid it.)

I've wondered if for example it even makes sense on a NNN retail building.Maybe if your CPA can do it cheap as part of their tax return service fee for you.Hopefully just your normal straight line depreciation is the way to go, but check with your CPA and see if they think it is worthwhile for you.   

I might suggest attending one of the local meetups, to be able to talk to other investors that are at various points on their journey.