These are great ways to present a property to influence a favorable appraisal.

Could limit access to favorable loans and insurance on a new primary residence in the future.

More often than not, these work in the favor of investors, often those properties aren't being used at their highest and best. 

Buyers should expect more competition in the spring, but conditions overall should remain favorable compared to recent years.What if I’m a seller?

Your lawyer's concern about the due-on-sale clause potentially disrupting your BRRRR plans is valid and could lead to less favorable refinancing terms if enforced by your credit union.

Update: In a more favorable market I would have waited before committing to this deal which I agree has some yellow/red flags.

You learn a lot by going through the motions.  

I understand that you want to look for a place with year round tourism, growing tourism stats, favorable STR regulations, etc.

Not the smartest move by the seller, but it cuts down on buyer competition, which is in your favor. include something like this: Offer is contingent on buyer walk through of the entire property within 3 days of acceptance to buyers satisfaction, otherwise buyer may declare this offer is null and void via written notice within 5 days after AO. 

I HAVE A BIG FAVOR TO ASK OF EVERYONE WHO HAS READ AND ENJOYED EITHER OF THE BOOKS: WILL YOU *PLEASE* LEAVE A REVIEW OF ONE OR BOTH BOOKS ON AMAZON.COM?