Facilitate conversation and get people to talk like adults.

The house has survived many hurricanes with little damage, but the insurance company said they would not renew coverage without a windstorm exclusion. 

This sounds like a good plan - sticking to the duplex or SFH for students is good too since most DSCR Lenders generally stay away from "student housing" but if you are looking to purchase a rental property that can easily be utilized to rent to any tenant (adult, family etc) including students, you should be OK

Hey, my wife and I own a variety of properties… warehouses, single family homes, self storage, commercial buildings, multifamily etc.
My son is turning 18 in December. He’s probably going to end up going to a trade s...

I have a HELOC in place on our personal residence and have used it exclusively for flips and spec builds.

@Jacob WohlgemuthHey Jacob, to @Manny Vasquez's point, whether she qualifies for the Primary Residence Exclusion or not will be the primary factor on your tax question. 

Hey, my wife and I own a variety of properties… warehouses, single family homes, self storage, commercial buildings, multifamily etc.
My son is turning 18 in December. He’s probably going to end up going to a trade s...

Despite offering almost every amenity for an ideal vacation, my efforts to increase bookings through more than ten non-exclusive agreements with local property managers and continuous outreach to travel agents have not been fruitful.

To me this makes sense because a one bedroom can host 1-2 people easily with a competitive ADR and cleaning fee, while 4+ beds can host multiple families and split up a higher ADR between more adults. 2 bedrooms can be price competitive with 1 bedrooms and attract the same guest avatar plus small families or 2 couples. 

Most fail to appreciate insurance coverage typically only covers negligence and any act that exceeds negligence is treated as an exclusion.