I feel like southern Jersey would also be a penetrable market to invest in so why not capital the opportunity there?

I think that moisture might be penetrating through the brick and mortar from the exterior or maybe the window.

When you are ready bring in a experienced licensed contractor.In my opinion, finding and fixing the water penetration points is you priority, it won't cost you a lot.

I lived in San diego for 5 years so I want the warm embrace of the sun for as long as possible. 

Before even thinking about doing anything aesthetically, have an inspector check the existing systems and structures, dig deeper, embrace patina then decorate with new old things.Goodluck!

Embrace that stuff.2. 

Don't fear it, embrace it.

"Subtle Art of Not giving a F*ck" by Mark Manson taught me to embrace the fear of failing and use it as a learning tool.

"Subtle Art of Not giving a F*ck" by Mark Manson taught me to embrace the fear of failing and use it as a learning tool.

Again this is a huge step, embrace this!