I might go around to several dealers and talk to them and see their programs and listen to what they have to say. After all they ARE the experts.
I just read on Thread time news a comment and chart listing the various differences between Embird and Designers Galery. You can see it at:
Hopes this helps answer your questions. I don't own one, but I understand that Bernina has a very good design program.
I have the new Husqvarna software and it is marvellous. So much better than previous versions and well worth the money. Expensive but worth every penny ( cent!)The total Professional package does everything but you can buy only what you need.
First question is, do you want autodigitizing or manual punch digitizing? Digitizing is the term used to describe making a machine embroidery design. Autopunch is very simple to learn, but delivers uneven and rather disappointing results. Sometimes it's ok, but often the design will stitch out with tons of (frequently illogical) jump stitches, resulting in a huge mess. Manual Punch means that you (not a computer program) decide where the lines and stitch points will go and in which order they will sew out. There is a much steeper learning curve with manual punch (as an example, it took me about a year before I was comfortable enough that I started to offer digitizing services for sale), but the results are so superior as to make it the only way to go. Because of that fact, I'm not even going to mention any specific autopunch programs.
I have heard good things about Embird, although it can be expensive, especially with all the fun "gotta-have-'em" add-ons they offer. There is also PE-Design, but I know next to nothing about it.
I personally started with Embroidery Magic 2 and then eventually upgraded to FancyWorks Studio. EM2 is pretty inexpensive (around $90), but comes with almost no documentation, so you would need to purchase a tutorial to go with it. I recommend Aunty M's, which you can find at www.auntymdesigns.com/html/embroidery_magic_2.html. She even has her own Yahoo!Group that she will invite you to join if you buy this tutorial from her, and she is amazingly helpful. Buying both the software and the tutorial from Aunty M will give you a good discount.
I hope this information is helpful to you.