I’m in the process of purchasing a second home in Aspen, CO, which will also serve as my first STR property.

If the permanent financing will allow you to recover most of your initial investment and the fair market rent covers the principal, interest taxes, and insurance with cash left over, you have a BRRRR.

This would apply to your unit.Your biggest concern with setting the rent should be the near future. 1) Your insurance is guaranteed to go up, probably dramatically.  2) You may get an insurance assessment bill to cover the CA Fair Plan losses.

I use a loan servicer who processes the borrowers payment and then sends to me.

So we created our system of fully designing homes before we ever swing a hammer on a project.

It also negates the need for insurance - although that isn't our MO. 

So, only chance in hell it has is via the BIGGEST action of it's kind EVER in US history, with coordination between the insurance carriers, and home owners.

And could even get a second home loan if doing traditional financing.

I’m curious: are others who house hack buying homes they can just barely afford, or are you sticking closer to the ~30% housing rule and using house hacking income as an added bonus?

If the other two parties want to flip a house maybe they can do just that as partners and then sell you the house which you can buy with a primary home loan with low down payment.