I feel that I already have an edge against the cookie cutter agent.

If you purchased a cookie cutter cabin though, you're going to suffer more than most. 

I work primarily in Marion County, so I am of course more comfortable with Oklawaha, Lake Weir, Summerfield and Belleview.There are still some deals that can be found around the outskirts of the Villages and you will never lack for tenants and/or buyers.I would stay within a 15-25 minute drive of the school, (in any direction) look for 3/2/2 cookie cutter homes.

Your payments on the combined rig will be way less I'm sure than your rent in the trendy neighborhood and if your work is 100% remote then why tie yourself down immediately?

They like cookie cutter, by the book deals that fit their box. 

This entire scenario is pretty much the cookie cutter example of most deals that I see.

It is not a cookie cutter answer, and really depends on the property, location and if you have consistent guest demand based on that.

As landlords, we have to throw away our cookie cutters!

Yes, we have used this strategy 3 other times and all 3 times the appraisal and refinance have went as planned.Two of them were 3 families in New Britain and 1  of them was a 2-family in Plainville.Those were cookie cutter multi-families though, but we deemed the potential cash flow from this property to be worth the educated risk of the potential appraisal issue on the back end.  

I believe it will be key to fast tracking this rig!