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.

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.

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.

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. 

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

Well at least that was a year ago.  

I have a PM for the property in my own town as well. 

It's tough when there is only one property of any type and multiple applicants so remember if it's not out of your scope to get them set in a right direction as well if there are multiple qualified applicants.Best to you Jake, stay safe!