DSCR financing is based off of rent/PITI and your credit score. 

I'm a former internet marketer and software engineer.

The builder will need to be approved by the Bank/Lender or the bank/lender can provide you an already approved builder they have used before in that County.Once the builder is approved the Bank/Lender will have a initial meeting and set up an agreed upon draw phase based on the work that will be completed in phases.Best thing to do is have a conversation with a seasoned Banker or Loan officer to start an application and set up step by step plan.Feel free to reach out if you have any questions I am always happy to help and talk REI.

I’m currently based in San Francisco, California.

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

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

With STRs this is almost impossible, because homes & ownership change all the time and there aren't any universal recognition points or services that can grade what you're getting.

Owners mistakenly ASSUME all PMCs offer the exact SAME SERVICES and PERFORM those services EXACTLY THE SAME WAY, so price is the only differentiator – so, they often select the first PMC they call or that calls them back!

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.

Depends on what your GOALS are. do you like not being tied to the burden of debt service every month & sitting on equity?