If you’re paying off more than $1,500/mo I’d probably keep it barring any major upcoming capex. (3-5 years out so buyer wouldn’t automatically ask for it to be repaired at sale.)Good luck either way. 

Some car companies don't allow transfers of their cars shortly after they are released.

That's going out and getting a brand new car with the expectation that you could sell a depreciating asset for more than what you paid for it.

Build savings through side hustles like flipping cars or offering handyman services.

The property manager can make or break you, it has to be a PM that is working in that space and is comfortable there.I agree with earlier comments to look in the front and back yards to see how many old cars, abandoned junk, or treasures that aren't treasures are piling up. 

I was wondering who I need to hire to get this space legalized for a curb cut to park a car there.

do you have issues with the city if there are cars parked on the street or lawn?

Oversized 3 car garage. 2182 square foot total.

I would look for a 2 bedroom 2 bath duplex with a one car garage for each side located between the two units and each front porch on the each end of the building.  

Your comment does bias me slightly in favor of Indy, since at least we're talking about a manageable car ride.That said, I'd love to know the biggest mistakes you've seen - how do neophytes typically "crash and burn?"