I spoke with the title company who is still helping us wrap up the set-up of a servicing company, and she confirmed that they would be responsible for the principal / interest for Nov and Dec, while we are responsible for the escrow shortage balance (as agreed upon).Not sure how it was missed - not my favorite title company to work with.

You sell when it fits with your original business plan (targeted NOI is reached, timeline is reached, etc.). 3.

I do not do a lot of volume, so it would take me a long time to get a good data set just based on those numbers. 

While using QuickBooks it is a mind set and you have to accept the process and procedures to use it as a real estate and property management software.

My goal is to be filthy rich and set my family up for generations. maybe I should pay the mortgages faster?

We can't wait to see these set up.

Does anyone have experience of setting up a STR while in the same position? 

I offer an online payment portal to submit rent payments via ACH or CC - they "couldn't figure out how to use it" so I set us up to accept Zelle payments.

Best approach is to have your "team" set, before going out to secure properties. 

@Zach Denny  Similar to what Minna posted above, I have done with a local portfolio lender bank where they set their own lending rules.