Max, buying through the SBO store is the main financing mechanism, but there was a "cap & burgee" sale over at the TrailerSailor site (added surcharge towards the updated software).
The new software has a bold newer look that some luddites may react to but on the whole it is a happy improvement.
I would think that CSBB could tailgate onto it if you all chose to. You should check it out. http://forum.trailersailor.com/