So, if I am to understand this, you can't break up a contract?
No a contract cannot be broken up into smaller increments. If you want sell it, you sell the entire contract. That's why people recommend if you want to buy 300 points to get it in 3 - 100 point contracts.
Since we are discussing it and I have no idea how it all works... is my contract worth less now that I am 10 years in? I believe my contract life is 40 years so it only has 30 left.
If you click on the ad at the top of the page for the TimeShare Store you can see a list of contracts for sale. VWL contracts have been listed any where between $59 to $74 per points. More money for smaller contracts as they are more in demand. I don't know what you paid 10 years ago so can't tell if your contract is worth less. But do keep in mind after staying at WDW for 10 years you've definitely gotten your money's worth and have a good chance of selling and recovering a lot of the money you invested.
Is it possible to do a straight up trade if I wanted? Exchange my 300 VWL for a 300 OKW? If I did that am I subject to the contract life of my trading partner or is there a reset somehow?