With this being an income-generating property that is cash-flow positive, this should not have negative long-term effects on you or the co-signer's DTI. 

I feel at this point in my life I get more excitement out of buying the next property than I would get just putting it into our savings or spending it on random junk. 

A couple weeks ago I built up the courage to walk into and random real estate office and ask the broker if he was basically willing to teach me the industry. 

Aquire a vacation house to use like 5% of the time but still have it as an asset generating positive cash flow and not as a liability3.

I went to Boulder city after the market fell and I saw condominiums that were listed for 150 000 that would generate rents of probably 12 to 1300 a month and those condominiums were selling for 50 000.

Your sanity and peace of mind will be more intact on that path and you'll also have more time available to keep on with certifications and eventually an MBA to boost your income even more.3)  Once the income stream ("just over broke" as Robert Kiyosaki calls a "job") is in place to generate much-needed capital, I would settle into a very frugal life to begin with. 

The new generation of Smartkey don't have the same flaws, but they are vulnerable just like any lock.

All of the units generate income, just not fast enough for the amount of issues we have had to manage.  

-One unit is generating a estimated cash flow of 2,000 a month after expenses.What are my best options?

I am emplyed as a Union Ironwoker and during my off season ( January and  February ) I decided to start doing handyman work on my own to generate more income.