So other than the Bay Lake points, we got in early with Old Key West (when it was the only DVC resort) and paid very little. We have taken many cruises that cost nothing with points, many Vegas trips, trips to Hilton Head, trips around the country (Poconos, San Francisco, Chicago, Washington DC, etc) using Disney points (you can easily switch some to RCI for just about any other resort). Because of this, we got our money's worth. Flash forward when Bay Lake opened and my parents went and bought more points. Now the annual cost is through the roof and with teenagers now, we aren't using them as much any more. My parents are getting old and they don't use them as much with their friends. My aunts and uncles and grandparents all passed away so they are not using the points "from beyond".
We buy food at the beginning of the week to eat some meals in the room, we never get the Disney dining plan (complete waste of money unless you eat at buffets everyday....just a side note on that, about 5 yrs ago we chose not to do the plan for the first time since the 80's when it was the "Gold Key plan" and for six of us, saved over $1600 in food and beverages for the week over the plan and we ate constantly)
I think it's worth it for those that have many people involved that can use it all the time. The flexibility of staying at any resort and any time in any sized room plus the discounts on food, annual passes, merch, free buses to and from the airport, pools galore, extra magic hours, etc make it a good investment .... if you use them all the time every year
It totally has and I got suckered into the conversation LOL ... I can talk Disney all day