4) Would time spent in Big 4 Real Estate Tax or Real Estate Business advisory come in handy - or should I skip that step and go straight to #2?

Frankly if you think something that unlikely is going to happen then skip real estate and just buy the lottery ticket, it is much easier.How can one get a 'real' private lenders to fund the deal or where can one get partners to partner or JV with the investor to do the deal and split the profits?

By skipping a mgmt company, I might free up enough cash to allow for some cash flow.

I've done something similar and you can read the story here... http://www.biggerpockets.com/blogs/7103-skipping-t...While in Orlando connect with @Andrew Davis.

Hope you are not skipping a huge tax-free gain by not selling this.  

I have heard of some people using a skip trace service along the way to find owners.

Applying that rate against the same dollar amount.Because you're doing the same second step, you can actually skip doing the DCF analysis and just compare the rates directly.

I started skipping nights and even one or two entire weekends.  

@Kelly BuckYou skipped many steps in the process already and now you're asking what a judge and/or jury would do/consider. 

Skip it.