As I mentioned, I want to get out of the corporate world and would ideally like to be able to do REI full-time using it both for income and long term financial security/investment.  

I would certainly do that if it made financial and/or life sense. 

So your debt is about 69% of value. 

I need to analyze my financial situation to see when is better to pay capital gain taxes on our rental property we are selling- this year or next. 

Personal finance, Real Estate Investing, these are vast worlds with many viable routes leading to financial freedom and many pitfalls to avoid. 

The ones that think they do are usually following the traditional BP model...and they'd be wrong.You have to "reverse engineer" it, starting from your Financial Goals, and working your way to where you are right now.  

I wouldn't be to concerned about your overall debt if it's from other mortgages. 

@Travis SperrI love to listen to his advice but I don't always agree with all of his investment strategies most of them come from his financial advisors.

I'm not trying to be a "downer" but... all these optimistic predictions from people who financially benefit from optimistic conditions in the market are a bit misleading. 

I bought this property at 23 years-old working as a full-time financial analyst in Santa Monica.