What i learned by personally speaking 1 hour with the billionaires Howard Marks and Alexandre Soares dos SantosAfter 2 years living of the proceedings of the sale of my previous company, about 200 books, personal encoubters and almost 30 direct interviews you come to the conclusion that you need to:1/find what people want and figure out a way to provide them that2/connect that with your interests so you can follow it with everything you got3/embrace your strengths and weaknesses and figure out a way to protect yourself where you are unreliable4/estimate the % of succeeding and the % of failing so you won't get burried.5/develop a plan6/assign the stuff to people like you that can get you what you need, treat them with respect and show them you are grateful for their work7/look for a steady recurring source of revenue8/sustainable steps.

@Tim Schroeder - Well, we think Colorado Springs is particularly strong because the city is 1.) embracing Airbnb and 2.) has strong appreciation potential.

If they do, they probably were not the best fit, or did not truly embrace the vision.  

You have to embrace this or if you don't, you will forever be stuck in no mans land when it comes to loans.You will need to show enough income averaged over 24 months that allows you to qualify for the loans.

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.