Jon B.Working with contractors without Insurance (General Liability and Workers Comp. at the minimum) is asking for problems:1.

He confirmed my assumption that the estimates on Zillow, etc. are pretty much junk, that they will regularly be at a minimum 5% off, sometimes much more, and that what he has seen in the past is that new investors have based their numbers (purchase price, rehab budget, etc.) on these inaccurate numbers and what started off looking like a great deal, turned out to be a bad deal for them after the actual comps,  inspection, and assessments. 

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Here's my assessment based on what you described. 

What I would do when beginning my journey is assess my current situation and goals.Are you open to owner-occupying your first investment?

Meet them in person and ask as many questions as possible to assess if you will have issues with them5.

Another simple idea is to just have an expert assess the condition of a few of the best properties you find with the original strategy. 

I'm not sure that someone's past performance in the market will be helpful if you are trying to assess your potential future performance.

Be prepared for this aspect when assessing and analyzing deals.

Got hit with a 24k assessment 1 year after purchase, but we are still cash flowing and got the condo at a great price, as well as at 3.25% interest.