Learning Curve -DS to Wilcom

I posted a while back about wanting to start my own home embroidery business. I've been looking for an Amaya because that's what I've been using for the last 2.5 years. I can't find one any closer than Illinois but I did find a SWF/E-T1501c for sale a few hours away. It comes with Wilcom 2006 software.

Has anyone here ever uses W2006 and Design Shop Pro? How do they compare? How outdated in the 2006? I'm particularly interested in lettering, DSP converts TTFs for embroidery (sometimes badly) does W2006?.

I pick up computer skill fairly quickly but it's always nice to know what you're getting into.