Since the original loan remains in the seller’s name, you may need a nominee interest allocation to deduct mortgage interest, as the Form 1098 will likely be issued to the seller.

For instance, said property manager manages maintenance issues, problems that arise during bookings, basically anything that needs a physical person at the property, while I manage the rest?

Landlord friendly laws keep you safe(ish) from legal disputes with tenants and there are pockets in both markets that are appreciating at solid or better rates.

You have a number of issues in your post unfortunately.

The issue I see is that market has historical appreciation below average (not bad, but slightly poor).  

All work done to raise value after TOD is not legally in that stepped up basis.  

There are cheaper one’s in D/F areas but I would be careful as those can create a laundry list of additional issues.

We have been audited by the IRS recently with no issues.

This second defeat at the ballot seemingly left WIP with few options, and it was looking like they way overpaid for this land that in it's current legal state could only be used as a golf course or park. 

A couple issues with Credit/income on paper.