The newbie Hump? What makes a Good Deal?

[Ibn Abney]

Hello BP,

Long time follower/listener, but new real estate Investor.

I am originally from Brooklyn, NY. If you know ANYTHING about real estate in Brooklyn over the past 20 years you know prices have surged tremendously!! That RE appreciation has taught me the value of real investing and long term profitability.

I have been in the corporate world for 8 years, I have a MBA, and own a home. At 28 yrs old I now realize the 401K and 9-5 job mentality will not get me where I want to go by age 50.

I have great credit (780+), about 25% down payment saved ($100K-$150K range), and a passion to invest (Stock Market has been good to me since 2010 :-) and taught me to seek long term gains). I now live in Chicago, but feel Out-of-State is best (I'm all about cash flow!!). However, due to large student loan debt, i just cant afford to make a mistake or lose money on my first few deals.

Any advice on getting past this financial fear and/or finding a "good deal"? I feel I am stuck in the analysis paralysis mode? Any advice would be helpful.