Literally just did. We initially bought in direct at $96/pt for VWL as a sold out resort in 2006 (at the 150pt minimum!). At the time everyone told us that was a bad idea, we should do resale, etc, but we were young and wanted the financing. Since then we've had 4 kids, and we've squeezed out as much as we can in a 1bed, and knew we'd have to add on to get a 2bed on a mostly-yearly basis. We had no interest in buying SSR/AKV, and no interest in any of the 2042 resorts (we already have one and we'll be only 60 years old when it expires), and CCV was out because we already own BRV. That leaves BLT (which I do love), and GFV (which I have very little interest in), both sitting in the $150-160ish range resale. We managed to snag the website error this past Saturday and get RIV at $169/pt, which is really a lot like our first contract where we could have paid resale at around $86/pt. This time we did it because we want to be near Epcot, and didn't want the resale restrictions - it was worth the roughly $10/pt extra we paid, and besides that we put the entire thing on our Southwest card, so the difference pays for the airfare, too.
I personally think it depends wholly on whether you still think a Disney vacation is worth it at all. My inlaws who have owned since '98 don't care anymore about the parks, they want it to be 'how it used to be.' I'm fairly certain that it's nostalgia glasses they're looking through - it's still just as magical now as it used to be, and for me even moreso with the over the top theming of Pandora, Galaxy's Edge, Toy Story Land, new Fantasyland. I'm excited to see what comes next.