I want to ensure I’m doing this the right way while keeping my finances organized and compliant with any regulations.

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 guessing that is because of your pessimistic view on the economy right now, but even if the markets dip temporarily, based on history, they will rebound to even higher points (I know just cause it’s happened before doesn’t guarantee it will happen again).Personally I have a successful business, but opted to diversify into real estate because my industry is heavily regulated and one change of a law could make me MUCH less profitable.

Real estate agents are not highly regulated in Costa Rica as opposed to North America.  

I’m slowly learning how to identify soil types but like you said….we can’t afford to be wrong right now  jurisdictions are different all over the US.. many still just use perk tests  others do the soil samples so you just have to deal with your current area and regulations.

One cabin owner I spoke with mentioned that even mid-week bookings picked up when they offered flexible check-in times and promoted the property as a remote work getaway.A quick tip: before committing, check Johnson City’s regulations on short-term rentals.

That doesn’t go unnoticed by regulators.

You need to check if the lease you created complies with any regulations of the area you’re in.  

It is a federal regulation but some states reach out and screw you.

The IRS has a regulation that amounts less than 15K are tax-exempt, of course, this requires you to file a tax return.