In general, if there's nothing in zoning or the deed restrictions prohibiting the division of the property, it's mostly just getting it resurveyed and presenting the new subdivisions to the local government (county usually) to have each lot recorded as separate parcels.

He did his time and he got off parole and has no restrictions.

Personally, I wouldn't spend money on an attorney because 1) I think the covenants/restrictions can sensibly be used against STRs and 2) because the HOA potentially has deep pockets if the officers decide to fight because they can pass the cost of the fight to the home owners.I would reach out to the officers to get their sentiments and to plead my case, and I would start building my case with the other homeowners. 

Disclosures, or other restrictions on transacting with homeowners.  

Euclid, Maple Heights, as far east as Lorain or even as far south as Akron?

I thought about buying it Subto, but she bought in 2022 at the height of the real estate market so the monthly payment is too high for this areas rental market.

That's going to require you to give a guest the login.Maybe I'm missing something but I couldn't figure out a way to give someone a restricted login to YoutTubeTV. 

In the Bay Area, most HOAs actively restrict less-than 30 days rentals in CC&Rs, and can have % rental caps on units which may make MTRs difficult. 

Otherwise many many many agents spend a lot of time and effort finding property and writing contracts only to find that the funds can't be transferred, or they don't have immediate access to the funds, or they need some kind of approval from 3-4-5th parties, or there are exchange restrictions, or 9000 other excuses.You probably need to find them a commercial broker who can handle whatever kind of investment they want to make. 

Great areas for cash flow and full to little rehab are suburbs like Cleveland Heights, Euclid and Shaker Hts.