Welcome Mark Walker - I've sold engineering software to Seagate, I'm a MF broker and investor.

The reason the estimates are so off on Zillow comes down to a matter of data completeness, and the algorithms used to select the right combinations of proximity, date sold, features, financing method, etc.

Since we are owner-occupied we have a lot more leeway in being selective with our tenants; but just for fun and kind of to standardize what we felt made a good tenant we created this algorithm.

That ultimate exit (bills/expenses) dictates the criteria for you property profiles, which then dictate the market you should be investing in.What works for me, what works for others, isn't necessarily what's best for you.In other words, you should be reverse engineering your plan.

Buy or inherit and hold all their lives while working the properties for income.I've seen teachers, firemen, software engineers and all sorts of people utilize both strategies successfully.

Jim Ingersoll, the speaker, was an engineer before turning full entrepreneur.  

Funny how all us tech / engineering nerds end up in real estate. :) 

We got an engineer to sign off on the foundation after we fixed the issues.

My background is in Engineering and Business but I have extensive experience designing and building houses.

In my opinion you need more of a creative real estate education on Power Prospecting - Contract Engineering - Negotiating - Creative Financing - Making offers - dealing with off market properties - Hybrid offers - Public Auctions and creating credit lines and cash partnerships - to mention a few disciplines .Baltimore is a small town - but there are a ton of deals that can be found when you go under-ground to dig them up -I would be glad to give you some referrals if still think you need an agent to represent you.