So I’m trying to see if I take that equity off the table and re-invest the sale proceeds in another market across more doors where we’ll see better appreciation, OR if we continue keeping it as a rental and work on principal pay down even though the rental price has been coming down and the home is not the easiest to fill because of the above average price for the C- to B neighborhood.Ultimately, my stated goal has been to build appreciation (over cash flow) by acquiring 1-4 doors per year for the next 10 years to allow my wife to retire (or be work optional) by the time she's 50.

@Kyle Carter we manage around 700 doors, with 92 of them being S8.When S8 applicants are properly screened, they can statistically perform a decent amount better than cash-tenants.

Feel free to reach out if you need anything while you are getting your foot in the door with real estate.

You're clearly a calculating risk taker, so keep working on what you know needs attention and those doors in the "wall" you mentioned will open.

You can throw some tenants in there, nobody is going to come there and lock your door.

I have one in Brownsburg that is similar, but there is a house and a converted garage on the same property. 

Does anyone have recommendations of what I can do or where I can look to get liability insurance? 

Some reasonable- a roof and ceiling repair from a major leak... some not so reasonable (they literally made me escrow the cost to add a deadbolt to a door).

I currently manage 36 doors.

Though we may come from a helpful place, we still get nervous talking to strangers, door knocking, or cold calling.