I haven't worked with this particular transition of PS to PP, however, I've worked with several others over the years and it is generally possible. I would suggest working with the techs at PrintReach/Printers Plan so they can walk you through the steps. Generally, you just export the data from PrintSmith and they might need to run a custom script to import the data and match the fields. There may be a one-time charge for them doing this for you depending on your contract, but it could be well-worth it to save you all the time of manually entering it.