I’m currently based in San Francisco, California.

This is the one question I’d add to your otherwise strong list of interview questions.- Doubling the penny every year for 5 years is really tough and really risky if it’s not your full time job.

DSCR if the house can support itself based on the lenders criteria.  

I think a daily allocation of 15-30 minutes for thoughtful communication on top of automations is probably a good starting point.An example that comes to mind is modifying an automated message going out for something personal that the guest shared with you in their communication so it has a warmer touch but the bulk of the lifting is still the base guest messaging.

I am based out of Janesville, but spend quite a bit of time in Madison as well.

This may sound crazy, but I own another STR in this particular market, and the reason I think this might actually be possible in based on the value of my other similar property.

It's good for segmenting leads based on criteria such as location, types of properties they are interested in, budget, etc.

Fees realtive to a low loan amount are always going to seem high - a lot of them are fixed and don't vary based on loan amount.

I would make the repairs, get tenants on track, and return it to the market while sales are still strong.

Although they are not Credit Unions- I am familiar with a few local lenders who can lend based on DSCR standards with a purchase price minimum of $75k (so  ~~$56k min loan amount).