I have MW II and I take lessons so I'm still learning. I don't find it intimidating but I feel like I still have a lot to learn. I haven't looked into Generations.
Hi Sewmom...it seems that the Generation software can do so many more things than offered with the MW II. If you get a chance Holly Pike from Artistic Threadworks gives 'free' lessons on digitizing with Generations. Which can be used with any software... I've taken many of her webinars and feel more confident about the whole process.
Go for it! I've attended a lot of webinars teaching how to use Generations and am pretty convinced it will be the software I buy.