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?

Start here...have a solid lease with an Addendum of dealbreakers/rules that are written in plain everyday language. 

I’ve fixed leaks, change toilets and still keep going up.I’m at appoint now when I moved out, I thought I’d be making money because while I lived there  I’d be going even.

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. 

Relocate existing kitchen to living space."

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.

I truly believe she had a medical condition and shouldn't even live in my house, should probably live in elderly housing or the like.

Hey @Spencer Cuello, so you will find most of us aren't fans of arbitrage.I see you listed NYC so you know that you can't do a STR in the city unless you live there.IE: You need to be onsite, living in the same unit you are going to rent.As per usual...

I'm more interested in purchasing 10 homes to have fully paid off by the time I retire, as I'm not living on the cash flow w/ current job. 

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