i was kind of in your same position only i'm a digitizer and not an embroiderer. i used the same software for the first 20 years, and then switched to Wilcom a year ago July. a couple of the reasons i chose wilcom was first, because its the most popular and i had clients wanting the native .emb file. another big factor is because of how it brings in a dst file. its much more editable than my old software.
as far as the learning curve...i had trouble figuring it out at first on my own, but i did go to the class in atlanta and that helped a good bit. when i got home from atlanta i did more simple designs in wilcom, but still reverted back to my old software, but i'd say that within a week i had it down well enough that i didn't need the comfort of my old software. after using wilcom full-time for a couple of months, when i would have to go back to my old software to make edits to designs that i had created there, it was really hard to switch back. i really had to think about what i was doing because wilcom had kind of become ingrained already. i do use the software all day every day tho.