My career has produced a resume that is full of contract work and intermittent short term permanent positions. Some of its a bunch of company transition (bankruptcy, downturns, and company relocation to other places) other parts of the resume are experiences that just were poor fits based on culture, environment.

Now you want to say:

My intermittent experience is a due problem but it has been steady employment with some fortune 500 and 100 companies over the last 20 years.

That's NOT the definition of "steady employment", that's the definition of either a job hopper or a problem.  While the bankruptcy, downturn and relocations are out of your control (except for your ability to choose a bit more wisely if you have several of these), the "poor fits" are all on you (again, especially if there is more than one).   

Then you say that you're getting mixed reviews within the industry as to the value of your degree, but you also now say that your degree is well respected and well received.  Really, you need to pick something and stick with it.  Either your degree is not adding the value you thought it should or it is opening doors left and right.  While a degree is a good thing, you have to pair it with comparable experience in order for it to truly pay off in terms of employment.  You can't do that right now because by your own words, your experience is a mess.  If you get in front of a hiring manager, you can certainly try to spin your mess with the line about a variety of cultures and product development efforts that I would never have been exposed to if I had been in a one dimensional job for 10 years, however, the bigger problem is that you're unlikely to get in front of such a person with the job history that you have.  Even if you do and even if the hiring manager agrees that you have a point, a HUGE issue for a hiring manager is reliability, stability.  We don't need to see people have been with a company long enough to get a gold watch anymore, but we do need to feel that you're going to last more than 6 months.  If you're going into management positions, we want to see that you're going to be there 3-5 years from now and then move up with our company.  That's why we're willing to invest ourselves in you.  If not, we'll move on to someone who can do that, even if they're got a little less overall experience or education. 

And while all of this may be true:

Because I am entrepreneurial, resourceful, highly trained in management practice and operations, I know product design and development like the back of my hand. I can make immediate contributions both technically and on a leadership basis, I am a spreadsheet wizard and can do some pretty nifty cost analysis and business evaluations, I am articulate and can speak in front of large groups of highly intelligent people. I can motivate and coach/teach people, I am honest and have legitimate integrity in a world where not so honest executives and managers have been making the news. I can make your company more profitable.

You're not going to do any of that for me if you only last 6 months or 9 months or a year.  If you want me to take you seriously, especially in a management position, you've got to grow up and hold a job for a reasonable period of time first.  If you were 24 and had a similar (albeit shorter) history, I could say "well, he/she was finding himself/herself, let's take a chance that this is the thing".  When you're in my age bracket I say "next". 

Does anyone have any suggestions about strategies in this job search and methods of breaking into management without being part of the "good old boy" network?

Yes, go into an entry-level management (or even non-management) position any way that you can and then sit on it for a couple years to help reduce the impact of the poor work history before trying to use your Masters and advance.

Again, I know you want to hear some sort of magic phrase or strategy that is quick and painless.  There isn't one.  You might trip over someone who knows you and wants to give you a shot by using what should be 20 years of industry contacts (networking) but you seem to have a disdain for that approach (again by your own words).  I have to think that if you had good connections from all your previous work you'd be using those instead of on these boards looking for someone to hand you a quick fix.  I'm afraid that further reinforces my impression of your short-attention span approach.

I'm telling you what any hiring manager would tell you IF they bothered to sit down and do so (which most don't).  I'm the kind of person you have to convince and from what you've got here, the only thing that is going to convince me that you've changed your ways is for you to prove it with a couple years in a job (any job). 

Tess