upgrade from DIY to either Expert or Commercial later (just contact their sales) once you are ready to calibrating customer displays..
If you were to go with the Pro versions now, I'd start with Expert unless you have one of the high-end meters (expensive) that Commercial requires.
If you want a Duo (I have one as well), that 2nd package you linked isn't that bad.. you may be able to call
them and work out a better deal including a VideoForge pattern generator and i1 Pro spectro (both can be added later) --- I would seriously consider budgeting in the future for a Spectro, at least the i1Pro... with any of the Colorimeters including the SpectraCal C6.
I'd say get a pattern generator, even if you decide to go with CalMAN and the DIY version (you need the Pattern Generator addon)... used Accepels are not that much when they are up for sale EDIT:
oops, that's right, SpectraCal changed the PatGen Addon and removed the Accupels.. boo
not an issue with Expert though
IMO You should know how to manually control the pattern generators and know which pattern is expected at any given moment anyways