Make sure it is a mature market (well established) that has friendly regulations where the municipality has already found a way to monetize through tax revenue.

One of the lenders I talked to this last week stated that with the new COVID regulations they wouldn’t be able to count my rent as income due to it not being signed to a year contract.We would like to buy a second property, owner-occupy it, and rent out the current unit we live in.

It would violate the State law for an unlicensed person to get a commission in the brokering of a real estate transaction --- its a regulated business. 

Costa-Hawkins forbid vacancy control, wherein rent is regulated when there's a vacancy.

That way you know the laws and regulations for the state you're in.5) Constantly educate yourself.

Maybe call the state board that regulates appraisers and ask them what they think of this practice and what recourse you may have. 

However there are also many areas completely regulating that out of business.

Make sure if you go that route, you understand your local rules and regulations regarding short term rentals before you jump in.

Well by 98 I had bought two more developments in Oregon as regulations at the time were a fraction of CA..

Lots of layout changes due to new regulations and all that.