They should go over the options, you have 2 (well there is a 3rd engineering level, but they wont sell it to you anyway). You probably want the standard, which is cheaper than the pro level. The only real difference will be ECM flashing. The standard will still allow customer parameter changes, full diagnostics and service routines, just no flash file updates, rerates, etc. We pay ~$750/year for the pro-version, I don’t know what the standard version costs, but it’s cheaper.
Well worth it, even for 1 truck IMO. You’ll be able to same quite a bit on DPF cleanings alone by being able to do the labor yourself and reset it in the ECM. We made the mistake once of having a dealer do one while it was in for warranty work and they charged us $1100. When we do our own, we pay $200 to have it air cleaned, with the gaskets, it’s still well under $300. It’s funny how I have always managed to work the temp sensors and diff pressure sensor tubes loose without damaging them, but the dealer always seams to break #### and sell you new ones.
Anyway, that just 1 job, as you learn, you can easily save more money by avoiding the dealerships than the software costs (and have less downtime).