Hello and welcome to the board!
I have both the Cricut Experssions and the Cuttlebug. I love them both and use them for different things. I don't use the Cuttlebug all that often for cutting, I wanted it and use it for embossing. I do have some dies that I got at really good prices though and now and then use them.
I use the Expressions a lot! And I really love it! Lisa is right the cartridges can be expensive, but they are often on sale. I have gotten some great sales on line and in the 'big guy' stores like Joann's, Micheal's etc. That being said, I must say that the dies for alphabets for the Cuttlebug are pretty expensive and you get what you see. With the Cricut you can change sizes to fit the project, with the Cuttlebug you can't change.
I think the Cricut has so much more potential for any crafter, but the initial investment is greater. But in my opinion it is well worth it.
If it were my decision I would choose the Cricut and if you can do it, go for the Expressions. It has a lot more features than the original Cricut has.
Like Lisa said Black Friday there are usually some great deals. I know my husband got mine for me on Black Friday and got a great deal which included 5 cartridges.
If you decide on the Cricut, just keep your eyes open for sales and also be sure to check out the internet.
Lisa did a great job of "outlining" what each of them is about.
Let us know what you decide, come back and let us know how you like whichever you get too. If you have any other questions be sure to ask, either now or after you get your machine.