Imagine how I would be structuring a win-win-win for all parties involved, using my marketing expertise and negotiation alone.

Your trying to create a win win for all involved and the numbers don't lie. 

Do you think successful RE entrepreneurs need to chase small time investors money, mentor newbies and write books about their winning strategies in an already over competitive / saturated market?

One of the bigger wins for me is the ability to duplicate listings fairly quickly across multiple platforms like HomeAway and booking.com, with an API integration you no longer need to use their admin screen and can do it all from HomeAway as well as process payments via Stripe.

I went to the steps probably 4-5 other times without winning anything.

You might have seen the soccer fans of the Mexican soccer team in the streets last night on your local evening news as they celebrated Mexico’s 3 – 1 win over Croatia.

Ringer's classic, 'Winning Through Intimidation'.

I hope it works out for you, sounds like you have a good situation: either way, you win:)ThanksBrett 

I assume both players have access to favorable debt, but if someone can purchase at a 5 cap, and finance the majority of the purchase with long term debt between 3-4%, the equity yields are actually reasonable and should grow (even modestly) over time.I am not sure if this answers the question, but I think what both groups are doing probably makes a ton of sense in satisfying the goals of their investors. 

@Mike Moles @Adam Negri is a TREMENDOUS real estate agent (broker actually I think), who just so happens to also be a solid player in the fix 'n flip business as well as long term buy and holds.