Assume my marginal income tax bracket is very high, and mortgage rate is 5.25%.

I believe that the Federal Reserve is going to cut rates by 25-50 bps at it's September meeting (no emergency cut), but that 30-year fixed rate mortgage rates will rise to upper 6s low 7s around the same time, and Commercial borrowing rates, including for multifamily, will increase as well. 

This home is not a luxury home so the insurance route seems overkill.2) Buy a worry free waiver and add it to the booking rate?

As rates go up, cashing out and refinancing is very unappealing.

For example we invest in mortgage notes so we have an AI agent that only scans the documents we have and lists and if we asked a question like "who are our top rates attorneys in texas", it will give me the results vs. having to search files.

It sets your expectation on the guest's rating and also tells them you care enough to make sure the stay deserves 5 stars. 

Competitive rates.

I understand that the investment or time and energy is required and correlates with success rate.

A FHA 203k Loan is where the purchase price and rehab costs are rolled into a single loan.Assuming you have a respectable FICO you can buy, with a FHA Loan (3-5% down, a 30 year amortization schedule, and a residential loan rate) AND because you closed personally, you will not have Asset Protection, in the form of closing in the name of a LLC/ LLC taxed as an S Corp, or an S Corp.

It's crucial to choose a market with steady job growth, low vacancy rates, and tenant demand.