For "just sailing" what you care about is whether you can get a boat in a condition that's good relative to the price you are asked to pay.
For the DSII, you can purchase Roger's book, which is a resource that doesn't exist in that form for the DS1. On the other hand, for either model, you'll get good support and advice from people in this forum.
If you have an actual choice of boats, then base it on your budget and the state of the boat, and whether it has a deck-stepped mast (the latter is easier to step, but sacrifices some performance - probably because it bends differently). (Mine is keel-stepped, and I ended up building a simple
contraption to make mast-raising easier, so even that is not a make-or-break difference, in my view).
You're probably aware of the danger of "analysis-paralysis". Pick whatever gets you on the water soonest! Good luck!