@Peter Neill First of all, that is an absolutely inspiring story and I want to say congrats and I best wishes for your continued success!

Over the past decade, the birth rate has dropped from 8.354 in 2015 to 7.016 in 2025, reflecting a continuous decline. https://www.macrotrends.net/global-metrics/countries/ITA/ita...4. 

You say things like "It was understood that I would continue to utilize the garage and one room for storage as I transitioned to living out of state."

(During this whole time I continue to market/show the unit.

What I would tell you is that as we built our portfolio we continued working our full time corporate (cubicle) jobs until we had 20 units (self-managing them along the way).

Although there are advantages to waiting too, such as if interest rates continue to drop.

- regional / drivable destination (I've personally rented out a bunch of Airbnbs here)- already established STR laws (while very strict, they have shown to grandfather in permits and haven't proposed a flat out ban that would also retroactively take away permits)- Fredericksburg also fights new hotels just as hard as STRs.

Whether you go with an LLC or continue to own the property in your name, having good liability coverage is always recommended.

I believe Hawaii will continue regulating STR and it will be harder to make the numbers work. 

I’m continuing to invest in real estate while also helping others achieve their real estate goals.