I just want to be able to rent my property out and have the option to enjoy it as a vacation home as well.

I am a BP follower and a real estate investor as well.  

Both my tenants (first and second/current) have been there multiple years each, young couples where one is a doctor receiving a housing stipend and the other spouse earns a healthy income as well. 

They do well as registered agents. 

Hoping to use the internet as a resource as well.

We are on the Eastern shore of Maryland as well :) We run the local REI (Delmarva REI) and have meetups once a month in Salisbury MD.

I'm hoping to have my Mom relocate there as well since SF seems to have a great community for retirees.

@Kevin McKittrick Well in my opinion an electrical upgrade should be paid for by the owner of the property.

I would say that you have a lot of opportunities for investing @Randall Alan explained well your financial strategies.With respect to what strategies to choose is depending on what you are willing to learn.STR depending the area is always a good strategy though you have to understand that is hospitality no real estate.Outside it will depend on the country and your knowledge.

You'll need to refinance out if that as well.