You can succeed without it.

I would try to leverage the inherent advantages you have being local: network with other investors and see what they are doing to succeed, become an expert in you local (or nearby) market, search out and find a great deal, consider house hacking as your primary residence initially, do some forced appreciation, self manage, etc.

And, given the lack of affordable housing right now in the city, is there any likelihood of actually succeeding?  

You will have to sacrifice a lot of your time if you want to succeed at RE with a full-time job.

All of these questions point to skills that are required to succeed as a wholesaler. 

They have people who are motivating them to succeed. 

Let's help each other succeed.  

I know if I succeeded I personally would be fine just throughputting somewhere in the six figure range.

You just described one of the key reasons why few succeed at real estate.  

Succeed and bring foot traffic and see your rents raised and the business displaced.