My consensus was...PROS: Higher gross rent potential compared to renting out the entire house to 1 person/familyCONS: Higher turnover, establishing and enforcing house rules, managing drama between roommates, more people to chase down for rent collection

If you have an established business, joining a new entrepreneurs group might not be as impactful (unless your business has something to do with these new business owners). 

For example, if you establish a relationship with a home inspector, maybe you could hire them for a small fee to inspect the work done by your contractor. 

I have plenty of clients that are mainly looking for tax advantages, so they don't care as much about cash flow as others might.Both Hillsborough and Pinellas have a lot of established areas that are good and up and coming areas that should pop in the next few years, depending on your risk-tolerance!  

What well-established big organizations try to squeeze out small business start ups like us in Boston? 

I also established a future decrease system with each new door I plan on buying in the future so that can factor into my analysis. 

Until you have an established book of business there isn’t really a need.

Most students heading into the Spring semester have already established their living situation. 

It looks like you established a "checkbook IRA" for the purpose of making the investment. 

Culture of the group - is it established & maintained?