If you don’t plan to sell the lots w/mobile homes is there a reason you have to split the lot?

I would both buy a property to get your feet wet and at the same time make a plan to scale.  

Stessa/Thread Bank APY is currently 5.09% so I actually make money every month even though I'm on the pro plan.

The best advice I can give is this: if you weren’t planning on RE would you go to college?

I plan to use it for maintenance requests, too, but so far no maintenance issues.

NOTE: we charge extra for this.4) What about a floor plan, so prospective tenants can get an idea where their furniture may fit?

If you choose to move forward, I recommend having a backup plan in case Hawaii outright bans STR.

It depends on the rental income, what you plan on putting down (20-25% is typical, 15% or 25% is required for conventional depending on # of units) For your owner occupied deal, you should be able to use a portion of the rental income to qualify and help offset your DTI a bit. 

I download those into Geo Batchcode so I can plan an efficient route to check out those properties, and of course I take note of any others of interest that I see along the way.  

They are holding the proceeds from my sale and I am planning to buy a couple of DSTs shortly.