First, I like the idea of bribery/guilt as an effective tool for getting what you want (trading DVC for something big he wants will likely work)
Next, the recommendations for renting points are great, as that will give your DH experience in what he will be buying.
Rugman does bring up a good point on the cost of the rooms over time. If cost is the issue, a comparison of what rooms will cost through CRO vs. DVC is a fairly easy comparison, and many people have spreadsheets if you don't want to make one yourself. Even accounting for annual dues increases, I feel DVC is a better value over time (decades). Show him the resale lists at a resort you like and emphasize the savings (if SSR has a low price he likes but you prefer BLT, you may need a small contract at SSR to start just to get in the door with him).
Of course, you could just have DH take you to WDW on cash a few times (staying at a moderate or better for comparison), take the room costs for the week's trip, and compare that to the price of a DVC membership to get a simply count of the number of times you'd need to visit to break even. Also keep in mind, the 1 bedroom and larger has a full kitchen, so food costs go way down if you eat in the room for most of the stay.
DVC Point Carts can be found at:
http://www.wdwinfo.com/disney-vacation-club/DVCpoints.shtml. Use these to caculate point total for a trip and multiple by $10 for a total room fee (no taxes).
As for touring styles, we take it very easy since becoming members. A typical day at WDW is like this (our real schedule):
- Wake around 7-8am, eat breakfast, dress, clean up.
- Hit park around 9-10am and stay until about 12-2PM
- Go to resort and have lunch, nap, swim, TV, etc
- Eat dinner in room and hit park again for the evening (around 6PMish - lots of people leave at this time for dinner, so parks are less crowded and hot)
- Return when we are tired.
- Some days we don't even go to a park, 'cause we know we'll be back!
If DH prefers a beach, you can stay in Vero Beach, FL, Hilton Head, SC, or (coming soon) Hawai'i. I would suggest introducing DH to one of these resorts (VB prefered due to proximity) during your next trip for a couple nights. You could then alternate years at WDW/DL and a beach resort using the same point totals. Options are great!
Lastly, be evil and use DVD marketing to its full effect. Have DH watch Disney travel shows with you, order the DVDs (especially the DVC one) and watch it a few time to "get your fix for free"

. Take a
DCL cruise as an alternative (the TV defaults to the DVC commercial channel and can be used as "background noise" while you get ready in the mornings/evenings - worked on my DW

). If you can get DH to tour, then the sales teams are pretty effective, too (but a bad guide to piss him off, too).
Good luck and may the pixie dust be with you!
