I am a painting contractor by trade and own a well established company.  

It will be easier when you have established relationships and have built trust over time.

Then, fly/drive to those markets, drive around the neighborhoods, meet with local brokers and start establishing relationships there.

Tennyson St itself serves as an outdoor mall type experience with various eating establishments and shops as well as multi-level multi-familes front and center to the action.

I guess trying to establish a team first and maybe that'll help dictate which market I finally land on.  

That might work better than buying an established one. 

Several articles were splashed which laid out stories about people returning back to the great city after hibernating in the suburbs for a few weeks and months and coming back because of hyper boredom and lack of access to shops and other establishments.

That is why I am a firm believer in establishing investment criteria and sticking to them. 

Old money, lots of farmers, already established.

I have a Solo 401(k) which I love, and was able to establish it after launching an e-commerce business much like @Bob Malecki suggests.