However, the units I see myself living in all barely break even on cashflow.

On the flip side, if you've got a bunch of Section 8 tenants living in a building that's in a neighborhood where a lot of the tenant base has good jobs, high credit scores, and are generally reliable people, you've got the most risky tenants in that tenant base and that ain't what ya want.

In my area these are rare so they are difficult to set market rent, and I imagine get a lot of wear and tear with a lot of occupants living there. 

While I currently live outside Portland, OR, I plan to begin investing in Tennessee.

I live on the main unit. 

@Chris Seveney  Good mourning Chris thank you so much for this response. what are 3 really good books I can buy for Commericial Real Estate investing (I have the millionaire Real Estate investor by Gary Keller), I've also looked at some CRE courses and I noticed some of them are asking for a bunch of money which kind of sketches me out, and about the military I was firstly thinking of  buying a 4 unit property and live in one of them then buy another a couple then with that I can buy a bigger property that's the idea I had in my mind because my father kept on telling me how CRE is only for rich people and it's risky but that's what I want too do .

I live in the Milwaukee area and want to get started investing locally but eventually want to branch out into other cities and states.

Our lot is fenced in and we cannot see where he lives but close enough to be of concern, but we want to stay in the same town until the kids are finished school.So, my question is this, would it make sense to rent our home (roughly $2300-2500/mo. as per real-estate agent claims), with the stipulation that the garage is used for my business AND buy a home nearby?

Quality tenants aren’t going to live in D properties.

@Andrew Katz, if you will be living in your next house hack, you should investigate a conventional loan instead of hard money.