Buying in those areas makes more sense for STRs as the municipalities rely on the revenue.Less chance of a lot of regulation.

However, a recent delay in its opening, now pushed to 2025 due to supply chain challenges and other logistical issues, has created a mixed landscape for real estate investors.Real Estate Growth: The Big PictureWhen fully operational, BlueOval City is projected to employ about 6,000 people.

Medford (North Boston) happens to be a low supply/high demand market so I absolutely need to get more comfortable with consistent rent increases but those increases need to be researched and in line with the market. 

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

Research local regulations thoroughly, as towns often require permits, owner occupancy, or restrict rental days.

Hey @Caprice Watkins, so Sheboygan does have some STR regulations. 

Part of this is regulations in my city, but after having done it this way, I wouldn't ever want to do it with a single family home.

Finally, The rent control discourages further development, limiting supply which results in higher rents.So rents go up, but the rent control advocates are too uneducated on the economics of the rent control policy to see their role in the rent increase.Another consequence of rent control is no value in keeping the property as nice.

I guess my challenge right now is to define the strategy and balance all the factors, such as job and population growth (value increase), cashflow (demand & supply market, interest rate, property tax, maintenance cost), and risk control (insurance etc). 

Likely they will only allow you to live in the property once you refinance out of the debt due to rules and regulations, but you can always ask!