I bought my CW back in April, and someone told me back then that they would eventually be selling the software seperately. As for Customer Support, I would expect that it would not change just because you bought it from Sears (IF that is true). I suspect that the staff at CW will still support the product as they always have.
As for the software issue, I don't see a problem with them selling it apart from the machine - I guess I look at it as a gain for me, having bought my machine prior to paying extra for the software. I think that the people like me have been in a "Betta" mode while they worked out the kinks. Sounds like things are about where they wanted them to be, in terms of performance, and now they are ready to take it to the next level. Good luck CW.
I guess if what you are saying about Sears is true, you've answered your own questions - if you are leaning toward purchasing a CW, NOW is the time to do it and save a few bucks on the Software. I don't think that you will go wrong with this machine - it does what they say it will do. Good luck with your decision, hopefully you will make the choice that is best for you.
Bill
As my Grandpa used to say "Suit yourself and let the rest be pleased!"