Ben-
Deeded weeks bought after June of 2010 cannot be enrolled into the DC program at this point. Maybe sometime down the road they will lift the restriction, but it's anyone's guess.
Resale points supposedly can be enrolled at a $300 per person educational fee and a minimum of $2000 as an enrollment fee. There haven't been any successful resales of points posted here, so no one is absolutely sure of the process and success, but that's what several people have been told. The documents give Marriott the right basically to always restrict usage of resale purchased points, so it is still a grey are. If you buy points resale make sure you are getting a really good buy since, imho, you're going into unchartered waters.
And I wholeheartedly agree about timesharing enhancing vacations with family. Our biggest regret is that we got into it when our kids were in their twenties, but have already enjoyed the benefits of 3 generation vacation, vacations with close friends, etc. Having the space really enhanced those family trips, and not having to start the day finding a place for breakfast was a big plus for us. Being able to invite friends to join us was great for them- and for us, and we all have memories we'll always cherish.
That's why I say the value of ownership is so much more than the dollar and cents calculations. While clearly you can vacation the same way without owning, the reality is that most people won't. Life intervenes and money is often spent elsewhere, and let's face it, we're less likely to rent a bigger unit to invite friends, but if we have one we're happy to extend the invitation.
LMT- if the upkeep isn't a struggle financially, you should really rethink things and see if you can get good use out of what you own without too much effort. There are a lot of people here who will be happy to give you advice and you may find that it is a great way to create lifetime family memories, and what better memories to instill in your kids than wonderful times spent with parents and loved ones?