@Jay Hinrichs exactly the risk is even more than traditional development and the profit is actually less with more operational headaches.

I talked to my lender contact and, as Kerry mentioned above, it's pretty uncommon that a traditional lender would offer a HELOC product on an investment property (non-primary home). 

Reason why is because FDIC Bankers "Do Not" charge points on traditional programs like primary homes, standard investment purchase and refinance, Second home/vacation homes.Lenders, Brokers all charge points to meet their Loan officer compensation plan (commission).

Based on your description, Party 1 seems like the safer choice.

That level of diligence isn't possible with human effort or even traditional data processing techniques.I would like to expand to investors in the future but this technology is very new. got it also commerical Brokers I suspect would be a target for you.. 

Whether you choose to run screening before you show the unit to them is a personal choice. 

So if, for whatever reason, laws change and you can't rent it out on Airbnb, etc, it still cash flows if you need to rent it out to a traditional long-term tenant. 

@Stanley Nguyen You can have an SDIRA despite having a 401k through your employer - it works just like a Traditional or Roth IRA.If you have SE income, you can have a Solo 401k, too, but you are subject to the annual contribution limits across both plans - your Solo 401k and your 401k through your employer.

Depending how much of the neighborhood is a hot zone for renting rather buying, and which Property type is performing better than the other (meaning 1bd 1ba 2 floor renting out faster and much more consistently than a 2bd 1ba 1 floor), you can make your choice of those factors as well as other ones that impact your decision for what you wanna do with your investment.

whats traditionally referred to as "DSCR" loans are not going to be eligible in non-state territories unfortunately