If you have the assets that cash flow is unnecessary, you can concentrate on total return without needing to focus on the cash flow.Cash flow is tough in the current market.  

I really appreciate the guidance on starting with house hacking and creative financing — it helps me focus on learning the fundamentals without taking on unnecessary risk.Your point about structuring deals with the tax and entity side in mind from the beginning is especially helpful.

The guests either says heck no I am not giving Airbnb money and reverse image search the listing to book direct or the guest (like me) hates unnecessary fees and books something somewhere else or not book at all.

This is technically unnecessary leverage since you can sell for cash with zero taxes. 

I am very dedicated and willing to put in endless effort to learn the ins and outs but this could expose me to unnecessary risk if I miss something.The problem with using an agent is that they will want 3% which feels like a large amount for a deal that I found and that I'm negotiating.

Failure to understand procedurally how useless these strategies are leads to a lot of unnecessary costs and time spent chasing down these strategies where time and money is better spent elsewhere. 

You'll lose your primary residence homestead exemption (which caps property tax increases in Florida), likely pay higher mortgage interest rates or struggle to get financing (owner-occupied mortgages require you personally to own and occupy), and create unnecessary complexity for minimal liability protection when you're living there anyway.

Anyone have experience with these policies—do they actually cover the big-ticket repairs, or is it just another unnecessary expense?

Between the two, you’ll cover the vast majority of guest traffic without adding unnecessary cost or complexity.

A loan can work if she prefers structure, with IRS-required interest, but she could forgive parts each year under the annual exclusion.For a one-time $200K transfer, trusts or custodial accounts are usually unnecessary unless her estate is near the threshold.