I've only had two cutters. The first was the Gazelle. Not to dismiss the experience of others, but that was the worst machine & customer service I've ever experienced.
When I was having problems I posted in their forums - 9 times out of 10 I got responses that told me that the machine was awesome (helpful how? implying stupidity on my part?). The help videos had no sound and the pop up boxes (with written directions) were often covered with the controls used to play the video. The software was wonky, often causing my laptop to freeze or blue screen. The "free" cut files included with the software were often incomplete (as in the cut lines didn't line up) and I was told that they *knew* that the free files weren't very good, but they weren't from BossKut so there was nothing to be done. The machine/software (quite literally) had me in tears more than once, and the c/s and forums made me feel like a complete moron. The most disheartening thing was that there were NO poor reviews. Everyone out there seems to thing BossKut is the bomb - maybe I'm just the odd man out?
DH finally sold the Gazelle and bought me a Cameo. Now, I don't know what sort of things you want to cut, but for me it was a fantastic solution. C/S has been all that I could wish for and there are a million clear, helpful videos posted on YouTube by tons of different users. Don't like one person's teaching style? Find another!
And yes, you do get a bunch of free files (with pretty much all cutters I think) but then you have to buy individual files from the store. Hmmm, not entirely true. I've done tracing with free jpeg/gif images from the web and it's worked amazingly well. And there are plenty of sales, clearance images and a free shape of the week (every Tuesday).
I think the first thing to consider is what you want to cut, then how important it is that you don't have to connect to your computer. It's a very personal decision based on your style.
Isn't it awesome to face a tough decision that will ultimately make you happy?