Quote from @Makani Donaldson: From what I understand, different islands or cities have different rules, and they are getting stricter.

I'm just beginning but am considering a bigger commitment in the next five years or so by accessing some or even all retirement funds to buy a building (I'm sure people have thoughts on whether or not that is a good idea!).

However, the road block I face is getting to a point where I think it’s an “ok” deal (meaning it’s not fulfilling the 1% rule, but more like 0.75% and little to no immediate renovation cost/typically a new build townhome) and then I start to question whether I could find a BETTER deal if I just keep looking.

The general idea is that you must acquire an interest in real property you do not already own, and since you already own the subject real property you want to build on, the transaction must be structured so that you are creating an interest in real property you do not already own (in fact, it does not yet exist).

Keep building, you’re on the right track!

Each town has different rules regarding rent control. 

Rule of thumb: I've been told "Never fall in love with a property".

Ok, but I mean is it against the rules?

Points I can roll into the cost and don't mind a buy down if necessary.My primary concern is the bleed rate monthly for the build, Airbnb stabilization and the year after while we season it and prep for final financing for long term hold.

I am still pretty new to the area but I am ready to jump in and start investing in multi-families in the Albany and surrounding areas.  Since this is something that is best done with a team of experts that know a lot ...