If you are single or a couple on the same page about house hacking, look for uneven multis.

There is a good reason why "tenants, toilets, and trash" is something a lot of mom and pop rental property investors/landlords/flippers are eager to move on from when they can!

I don't think you are going to be able to get insurance for two separate living units in a single-family when they are both illegal and likely do not have the correct egress windows (basement) for fire safety which could subject you to huge liability if something happens to either party.

In Ohio you can find a lot of single family in the $100-200k range or 2-4 units in the $150-400k range that do pretty well cash flow.

You really don't know a single thing about Real Estate do you John? 

Didn't appreciate it would have to be that many doors multi-family vs higher value single family.

Then later on purchase homes with cash (single family homes), I would like to learn how to read the market and know where a state or city is thriving but also learn where it's not.

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House hacking seems like the best strategy for me.My goal is to purchase a single-family home in Maryland, D.C, (from lurking I've heard D.C was terrible for investing) or Virginia with multiple rooms where I'm making monthly payments similar to what I pay in rent and other charges ($2000-$2500).

if its a single family you'd get an appraisal called 1004 as is + arv . if its a 2 to 4 unit you'd get a 1025 as is + arv appraisal .