Lastly, the cost to fly to visit a property that most people can afford ends up being cost prohibitive.

All is well till the local authorities prohibit their STR or a bunch of people start STR'S in your location.

I, too, have considered building my own, but (1) I want to start/grow my RE business, (2) the cost of these services isn't prohibitive. 

Interest rates and loans down there are to prohibitive.  

I am researching on how I can rent out single family houses by the room but it seems like every single HOA rules and regulations prohibits this.

Defiantly hope the town agrees to it , I’m not trying to create anything ridiculous, but I think sprinklers would be cost prohibitive, and additionally difficult as one of the units is rented. 

I've read a lot about these tools, especially the prohibited transactions.

I think the risk of you having a prohibited transaction (extension of credit and not using a nonrecourse loan) is the real issue and not necessarily UBIT.  

The approval letter from the seller’s lender is for Only the buyer name on the purchase contract, no assignments and double closes are often prohibited. 

one thing to note is that interest rates on DSCR Loans (very common option for STRs) in Alaska are going to be a bit higher than most other states since the state has a prohibition on charging prepayment penalties (one thing to note if you are exploring this as financing option)