OK for what it's worth, this newbie will toss his thoughts in here. Remember I am a newbie with a CX2 so I'm dangerous (but having lots of fun). I took your criteria and modified things. Here it is:

Objective
Determine what to buy, where to start, and what to get next?

Assumptions
Willing to practice.
Will purchase or download a simulator.
Possess average mechanical aptitude.
Little or no prior RC heli experience.

Suggested Dimensions/Criteria/Input
NATURAL PHYSICAL ABILITY This is important, but how to assess? Suggest go to LHS and use sim there.
TOLERANCE FOR DAMAGING YOUR HELICOPTER Important and related to ongoing funding.
DESIRED END RESULT The goal is key.
FUNDING Both initial capital outlay and ongoing maintenance and average cost per crash.
FLYING AREA Both size and average wind conditions.

Removed
RC HELI EXPERIENCE Covered under assumptions
MECHANICAL ABILITY Covered under assumptions
WILLINGNESS TO PRACTICE/SIM Covered under assumptions
VANITY Not sure this is relevant for the given objectives.
GEAR THE FLIER HAS or WILL PURCHASE - not relevant for the stated objective. If the newbie doesn't have it, the newbie will buy it. If the newbie has it, the newbie can deduct that from cost.


Hope you don't mind the sudden changes in direction here but you are quoting Patton, so I figure you'll take this as constructive criticism/help.

Also, since I'm a newbie and since I've already bracketed my likely next step, I'm more than willing to be your guinea pig on the tool. And again thanks for building this thought experiment something good may come from this!!

Mack