Longest Distance to Self- Manage First STR?

[Bien Nguyen]

My husband and I are new to Bigger Pockets and have been wanting to own an STR and Bed and Breakfast in the future. We have goals of obtaining and running 3 STR's within 5 years or less as we both work full time, and I do real estate in addition to my full time job. We have a goal of buying a STR by the end of the year if everything goals well.

We have been looking at different properties such as cabins and homes in North Georgia that area close to wineries, outdoor activities, and state parks; as well as beach condos in South Carolina and Florida.

However, we are struggling with whether our first STR should be close even if the numbers are not as strong.  My husband is concerned about the distance and he is particular about maintenance work/ renovations and wants to be close where he can drive to check on the property.  I, on the other hand, am more about the cash on cash return and believe we need to focus on a good market as long as it is within the state of Georgia (we live in Savannah area) or within a 2 hour drive if out of state (like South Carolina or Florida).  

How did others start and did you buy a property that was close as your first STR?  Thanks in advance for your feedback!