It is very helpful to help me in my decision.

Nobody is selling anything remotely as useful and most online courses are some book they cobbled together borrowed from a site like Biggerpockets --  Only then to sell you for a  fortune.You already made your first great decision to question the material in a post....Wasn't that easy? 

Approach it as a business decision.  

You're left with the decisions to either:1.  

I was able to find a couple contractors who saw the benefit of working for me year-round (at a fixed rate), but the rest of them wouldn't come off their market rates in the summer months, so they only worked for me during the winter (at about 1/3 of summer rates, because they were all fighting for the work).Again, that's certainly their prerogative, and it's not my decision what they charge or how they run their business, but it meant that volume didn't play into the equation. 

Account ClosedI'm not a tax accountant so definitely talk to a knowledgeable one before you make a final decision.  

Outside of real estate investments we are a strict Dave Ramsey no debt household so this decision seems counter intuitive to everything we've worked so hard to accomplish.  

I also run Software for a company out of San Diego, California, and my business partner and I own a freelance Software Consulting company.I have been interested in real estate investing for a while now and am just now taking the steps to educate myself so I can make the best decisions possible. 

Trying to make this decision now, so would really appreciate all your help on this.Thanks in advance

@Brian Mathews @Jacob AndersonThanks for the suggestions, I'll be working through my final decision in the next week or two (June 7th I hope to get City Council approval to begin).