My initial angle once I do enter the investment world would be probably along the lines of what @Scott Nipp was referring to with generating seed capital before pursuing other endeavors. 

The son's attorney should be able to provided the best guidance, rather than some random guy, like me, behind a key board.Okay, well the random guy that posted above me, at the same time, may have better ideas than the attorney.

It does not surprise me that the younger generation is going through a major re-thinking of the owning/renting equation.3.

It's true that you can't depreciation to generate a loss in a given tax year.

Only issue is that if I transition out I need to have a W2 job that will still generate a steady income while I begin the path to real estate investment.

Like @Doug McLeod  mentioned above, my attorney stated LLC's just generate a lot of extra expense and paperwork, and recommended to me just to use an umbrella insurance policy. 

I would figure out what path will generate the largest profit (or smallest loss) given an amount of effort you're comfortable with -- then do that.Of course, this is something that you should have figured out BEFORE you placed your bid...what makes you think the deals are profitable if you haven't gone through the exercise of analyzing them?

A C-Corp generates accumulated earnings and profits. 

Lead Generation: I have been looking into a few different places to begin my wholesale lead flow.

So as registered agents, these are Businesses that Incorp Services, Inc. represents.In several dozen random views of filings for companies represented by Incorp, several "foreign" (meaning out of state) LLC formations do not list officers.