You don't "need" a property manager, but managing out of state would not be an easy task especially as a first-time investor.

As I understand it, there used to be an on-site management company that operated some of the units as a condotel. 

For a home, that's going to be an easy conversion.

Panamanian coffee is supposed to be great.

A DSCR (Debt Service Coverage Ratio) loan may be an option; certainly for the one that cash flows, and possibly for the other based on lender and rate at the time. 

For example you can build an ADU to rent out as an STR and stay in your main house, since this is still your primary residence it seems that would be an allowable use.

As an investor that is WAY too early and extremely complicated to achieve the transition to a Title.If you guys need a call with me to clarify anything let´s share a virtual coffee (or beer, depending on time) and talk some Real Estate.

@Taylor Cook, first off you CAN'T be an agent for the seller and also be the buyer!

The only thing I would anticipate needing in terms of capital expenses in the next few years would be a new HVAC unit which is on the older side, but we have already budgeted for that and have a service contract with a company that manages our HVAC, water heater and oil tank.Am I crazy for thinking that a property management company would be an unnecessary expense in my case?

It would be an investment property, depending on the property I would like in it or stay in the investment property I’m currently in.