I don’t believe any jurisdiction is getting more lax on STR regulation.

As always, some bad actors cause burdensome regulations for everyone else.Per the Akron Cleveland Association of Realtors:"For example, in Cleveland, a local agent in charge must be identified if the property is not owner-occupied.

There are opportunities out there but some strategies are risky. 1 - Airbnb (STR) comes to mind - very competitive, very saturated and becoming highly regulated.2 - Most STRs are transitioning to MTR so that market will be saturated soon if it isn't already.3 - Insurance crisis in florida is getting bad so those costs will eat up cashflow and short term appreciation.

Investors should familiarize themselves with local laws and regulations surrounding pre-foreclosures, as these can vary significantly by state and municipality.

STRs are an option too, but you’ll need to navigate stricter regulations in some areas.

And the locals in Highlands have been fiercely debating STR's and regulations for the last few years, so I wouldn't be comfortable buying there.

If it's just slapped in the backyard, i'd imagine it may not make a big difference but if you create an environment around it, it could be different.   

Keep in mind local zoning laws and market conditions in Portland versus Salem—Portland might offer higher rents but stricter regulations, while Salem could provide better cash flow opportunities.Your design approach has proven successful, so continue focusing on appealing upgrades like kitchens and bathrooms, but prioritize cost-effective and durable materials for rentals.

I'm seeking to be in an environment with like minded individuals to learn and network to grow my portfolio and eventually network to collaborate on larger deals once I have a better understanding of the commercial side. 

Situated on a 0.52-acre lot, the property provides a spacious environment.