However, the market is competitive, and rental regulations are becoming stricter.

Best bet is to carefully analyze the zoning maps and regulations or just call the town and ask.

Ensure that you check your state's regulations and requirements regarding security deposits.

@Wiley Hood to be honest, with all the new regulations around documentation for cost segregation that has come out, I recommend having a professional do them.

Issues with multiple national carriers leaving the state completely due to state regulations, massive loss ratios, huge increases in replacement cost values/limits due to inflation, etc. 

There is a lot more state regulations and lending laws change when 5 units or great.

Hoboken has stricter renting regulations than Jersey City.

We try hard to follow the regulations, including the Dodd Frank Act.

This is related to lending laws/regulations created by the Dodd-Frank Act in 2010.

In my experience, a property with multiple cottages and outbuildings can provide all kinds of creative strategies...some folks try short-term rentals or even specialized retreats if local regulations allow.