I would not purchase property on Martin, Barbour or equivalent streets as I down own enough magazines for my glock

My quick and dirty due diligence, for what is worth: Jon seems to have had a long and successful career on wall street. 

Easy Street Capital?

Added off street parking!

A similar house (in a worse town) rented for $1.91/sq ft a few months ago according to a Rentometer report I ran - we're currently listed around $1.52/sq ft.A home on my same street was gut reno'd and currently rents for $9,500/mo (smaller sq ft).But if I check Facebook Marketplace for homes in similar towns (similar beds and baths), the premium is much higher - towns like Lexington and Newton are more like $2.50+/sq ft, for much smaller houses. 

I have a sweet 1 bed, 1 bath unit with off street parking. 

One of my favorite things to do is ask local investors and agents: What’s your favorite street, neighborhood, or city to invest in—and why?

We couldn't go play in the NFL if we wanted to, or the MLB, and we couldn't walk on a movie set and act or go work on Wall Street. 

There are locations where even commercial space on "main streets" as you describe are difficult to lease or costly to fit out for tenants.

We saw an opportunity in an up and coming street in our local community.