The fact the you are asking this question for your friend is exactly why so many blue collar trade owners go out of business or struggle for ever.

Investors trading flip houses back and forth etc.

Short term stock trading/option trading is a completely different animal.  

I don't want to end up like most people I know; trading time for money, only looking forward to weekends off, missing out on my kids' lives to punch a clock or living a "comfortably miserable" life blaming someone or something else for my lack of ambition and success.

The problem was that while we were swinging a hammer multiple deals passed us by.

Even if you don't "swing the hammer" yourself you will see what goes into different elements of it through your contractors. 

I have been doing my due diligence on REI for a few months now and figured it was time to swing the bat a few times, or more.

She specializes in redevelopment projects, initiating and coordinating with architects, subcontractors and trade crews to execute projects on site from initial concept to completion, while meeting time, labor, material estimates and projects specifications.

I am a 18yr+ construction Tradesman with multiple professional trade level experiences Carpentry (Framing/Finish), Painting, Flooring, Total Drywall, Masonry, Concrete, Electrical & Plumbing. excluding HVAC & Carpet.. the other trades I get it done correctly w/o having to redo work, I like to do my Projects on time..

I'm not a contractor nor have I ever worked a day in my life in a labored or trades profession.