Chicago, with its vibrant neighborhoods and strong rental market, is a prime location for this strategy.

Unlike most dynamic pricing tools that follow traditional pricing strategies, Nightpricer employs an ADR-based approach, which adjusts pricing based on the actual daily rate trends.

I think that strategy works best in higher areas or mid term rentals near major employers.  

There are so many great strategies to help you scale your portfolio, so I understand your desire to find the right plan and avoid mistakes.

I have never done lease options before, but I do want to try the sandwich lease option strategy.  

I used to do BRRRR strategy here but now only do flips and help with others' house hacking or flipping.I had to move my BRRRR strategy side of the business to Tyler Texas.Are you still investing locally or only out of state?

Depending on your goals and how you are buying your properties you may notice that certain areas are difficult to cash flow in NH depending on your strategy and what type(s) of properties you are looking at. 

It would be wise to ask your CPA the capital gains exposure once this strategy is being executed.

I'd argue that there are very select zip codes where this strategy works.

If you ever want to connect and go over your goals and swap investment strategies, I would love to do so.