There's a lot to unpack as far as your specific situation goes. 

We try to be as proactive in our learnings as we can but still have a lot to learn/experience. 

I actually mention Bronzeville a lot to not only newer investors but even experienced investors as well because Bronzeville has become a very marketable and investor friendly area.

There is a lot to learn and no easy short cuts, get busy

Between the Universities, incoming Casino and Convention Centers and current state of the housing market there are a lot to be optimistic about.Shoot me a DM if you would like to connect. 

The comps are in the high $190-$200K but are complete remodels. ( All updates) Based off these numbers it wouldn't benefit me a whole lot to sell it. 

I would think by platting a parking lot to someone’s property for instance, would it not become theirs to do with it as they wish?  

You have hit the JACKPOT of resources for real estate investors.

After searching on Redfin for months for a 4/2, (I had my heart set on going bigger to begin with for rent stability, and long term, we can grow in to this house and not have to uproot)I'd always find something I didn't really like, from small lot, to HOA, Price, small SF, too nice, too far gone, there was always something to sacrifice.

There is A LOT to it that you will not find out about by just managing 4 SFH units.If you find that you are good at it and love it, then great, but be diligent and do some research first.