ALl that work and he is back to square one.I feel so horrible for him because I know how hard he has worked, and put the money he has been earning into buying this equipment and the trailer instead of wasting it on video games, etc.

Not that they don't earn it, just so you know. 

Based on your savings, what will you be earning/saving per hour?  

Whether that be a direct job change, or if you are earning well, start investing and get some properties that can help provide additional income which can help in that process.

Also, I have questions about how to collect and report rent earnings since this house is in my name as it was when purchased and not in an LLC.  

I'm a broker and not a principal so my motivation for taking the course may have been different than yours, but the vast majority of individuals who have gone through or have earned the CCIM designation are brokers and based on the course material I can understand why.I've been running fairly complex analyses of investment properties for the last year so I've gotten quite comfortable with the numbers for my market and coming up with a fairly accurate opinion. 

I didn’t have much money left, so I borrowed against my 401K and used my measly paycheck earnings to start my marketing machine going.

Though I wish I could go all in, it is not practical at this stage.For example, if I chose 100%, it would take 10 years of earned income and lean living to buy 5 - $50k properties.

They all rent for about 1000/month.My monthly PITI is 2800.00I add in my snow, building electric, oil on two of the units ($1200), water/sewer ($1200) etc and I come to a yearly expenses of 37,000.It will earn 48,000 in rent plus about 1500 in washer/dryer fees.So I have a cash flow of 12,500.

We heard that BPOs are a good way to earn some income while refining one's ability to value property.