Do you have buyers? 

Good for the buyer who would otherwise pay out of pocket to close, and good for HMH which gets the property at a low interest rate.

but it sounds like your mind is made up on this mentor.. flipping right now is a pretty tough gig for a beginner depending on market. very low inventory then sky high rates for your buyers. so use caution be careful also make sure you have a GREAT RE Broker who knows the values and what you should and shouldn't do in the rehab to maximize your returns. these things are very market specific U simply need to make sure your matching what is expected in the market you choose.. 

I'm VERY new to all of this, I don't have much of an idea on what contracts to use, to use or not to use an agent in the process, typical deposit I should put down while finding a buyer, etc.

Now if buyer fails to make payments it would be good for Buyer to deed it back to the original seller. 

Question: If you were to purchase a STR to close in November and the seller negotiated that the buyer must honor existing rentals with the current rental company/property management until January of 2025…. 1- does this negate the short-term rental loophole for the 2024 if you aren’t managing it yourself for these months in 2024?

Failing that, your next option is to lean on your existing lease which appears to have two sections that disagree.

Most buyers I've worked with are happy to be within a half hour to the beaches, which these towns are.  

In fact, we just closed a new buyer on a beautiful turn of the century duplex in Duluth allowing him to househack the upper level. 

Those buyers ended up backing out during the due diligence period.