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

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

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

They do well as registered agents. 

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.

In this episode it talks about rental arbitraging many units in apartments and then being awarded government contracts where you house a large amount of government employees  and the government pays you well over market rent.

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

Have not had a 'issue' selling in the past five years..I would say the additional development cost of an extra bedroom/bathroom are probably well worth it in the long run..Good luck. 

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.