I too have the same toys as you Dina! The jukebox is necessary if you want to cut images from more than one cartridge without switching the cartridges in and out of the Cricut itself. You simply plug the cartridges into it, and the jukebox to your machine. You are limited on the amount of cartridges (6, I think!) I consider it a step towards the Gypsy.
I forced myself to learn the Gypsy but loading ALL my cartridges on it and taking it without the cartridges to a weekend crop. I found it is very convenient and much easier that toting ALL that stuff. The Gypsy has a small screen, but gives you the capability to place, flip, resize, hide parts, join images, from each cartridge you have loaded on it. I personally like it. You can join letters (like the script font) to make a one piece word.
I do wonder why it has been discontinued though...maybe because of laptops, and the new Craft Room software...I'm not sure.
I would visit the cricut.com site and play around watching videos etc. YouTube also shows many videos if you search on Cricut Gypsy. Some videos will have some strong personal opinions, but I have learned you need to play around and find out for yourself if you like it or not.
Cricut support can also probably answer your questions about updates if you call and tell them what kind of computer you have, is it a PC with windows or is it an Apple computer. They can probably walk you through more technical answers by telling you what to click on, etc. You don't have to be a computer whiz to call them--that's what they are there for, right?
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