I am torn between pricing rent lower with a minimum 3 night stay or just weeding out the less desirable/more work clients with higher pricing.  

A property near the 606 Trail in Logan Square could command $2,000/month, while the same unit in a less desirable area might rent for $1,300.

This concept aims at addressing the challenges of what to do with defunct suburban malls and maybe even empty big-box retail store spaces that are in desirable and affordable neighborhoods.

If you're going to reinvest the proceeds you might want to consider a 1031 exchange or a cash out refi to generate the investment funds you desire for your next project.

Which is why I pay more, for less cash flow in highly desirable areas.In high income areas, rent is a lower proportion of income so therefore your tenants have a higher capacity for paying higher rent because rent is less than 20% or even 10% of their income.

That also makes that scenario less desirable.  

Is it better to have a job or business that is doing well, then funnel the money into larger projects, if my desire is to be one of the main GP for like 33-100 unit multifamily projects?

Your first step is definitely learning about the markets you are interested in and figuring our what your desired end state / goal is that you are hoping to achieve through real estate.

Over the years, we have built quite a network of agents that bring us quality off market properties in the areas that we desire.

If you buy in a prime location with desirable amenities, you’re setting yourself up for steady income and long-term growth.