To Upgrade or not?

So I Currently have a Singer Esteem and am having issues with it. It skips stitches and the buttonhole is worth beans. It does not like heavy material and eats softer, silky fabric (in comes the walking foot). When we purchased it we knew nothing about machines. Singer was a brand name that was well known for years. It was associated with quality and durability. We had bought cheaper machines and returned them within the same day. We thought the $350 investment would have been worth it. We thought we would be happy with the machine for years. 

 I just received my Husqvarna HClass 200s overlock. I bought it from Excelle. They offer lifetime free classes on the machines when you buy it from them. Plus you get a free membership for the fabric store located in the same shop, Club Tissus. I have a membership at Fabricville and KwikSew online for club BMV. Do I really need another membership? Sure, if it is free. 

The classes are worth a goldmine. Plus Simon really wants in on it as well. 

Now for the dilemma. The sales people are very good at their job. She suggests I buy Janome Memory Craft 6600p for what I want to use it for. She says this machine will take me through all my projects and last me a lifetime. I want to sew silks, stretch, bulky fabrics, duck cloth, denim, fleece, make buttonholes, I want it all! I do not want a machine that will balk, that will fault, one that is made of plastic. And I do not want to outgrow my machine in record time. 

I like the auto thread cutter, the 9 inch arm space, the integrated walking foot, the start/stop button. the buttonholes (OH MY!), the Knee Lifter (I could have used this!), etc etc etc. There are 163 Stitches across 4 modes, 7 one-step, sensor buttonholes, Block and script monogram stitches, AcuFeed: Built-in layered fabric feeding system, Jam-proof, magnetic, top-loading, full-rotary hook system.. I mean the list goes on and on (6600p) The question/dilemma is do I upgrade at the moment for something smaller/less expensive and then upgrade to this in 5 years. OR, do I bite the bullet and just go for the Cadillac for my second machine?

Oh, and it comes with the table! ARGGGHHHH! Decisions, decisions. If I wait there will be no more left. Then would I upgrade to the newer model? Is the new model better? Or is it made cheaper?