However, I believe I am at square one and need to put the time in that space first.

A ton of space. 

Thus far, our business has primarily been long term buy & holds in the lower income space.

Why not use this time to build a rock solid foundation for your future:- If offered, invest in your 401k up to the employer match (never turn down free money)- Save up enough cash until you can get into a solid investment (one that allows BRRRR or a hack or both)- Use the extra cash you have each month to tackle the projects/reno... if the purchase allows for a hack you can create a new rentable unit first and then use the extra income from that to do the rest of the project/remaining spaces.- After completing the remaining project rent out that space, go after your refi (which clearly has a lot of equity now because you did the work yourself, added income creating units and without pulling another loan... and you're ready and in a fantastic position for the final R - repeat!

So your monthly payment will be higher on a similarly priced home in Nashua vs Lowell (in your example).On the flip side, the Massachusetts markets tend to do better in downturns and recession, at least if 2008 is any indication…Other than that I think markets like Lowell and Nashua have a lot in common, in the multi family space.

Orlando and the space coast is where i have found investments and reasonable amount of visitors willing to pay rent weather it is the theme park workers or visitors.

If you don't own the lot, you will be paying the owner of the development a space / lot rental fee. 

Pro-tip: Find SFRs with multiple living spaces (ADUs/mother-in-law suites) and house hack those.

That back door is kinda floating in space now, so it should be fine.

https://www.cpr.org/2021/05/27...In Summit County, and communities surrounding Frisco, there have been some recent developments in the investment space to address the workforce housing issues by limiting Short Term Rental licenses, saying that will restore more community feel and provide more supply to workers and long term renters.