Man, I am all over the place.
@Girlstar30 - I say this in the most loving way possible, I feel like I am rivaling you for how many times I am thinking about changing my mind

.
I woke up thinking, ok, SSR really doesn't make sense. You just don't get anything from SSR points. You can almost always stay at SSR with other points. The only real reason to own there is for a cheaper way to acquire points. Sure, I like SSR and wouldn't be unhappy staying there. But, I can probably say goodbye to 2 BRs at CCV most of the time. And holiday stays at CCV. And WL is a much more incredible resort than SSR - it just is, IMO.
I also keep trying to tell myself, direct points don't get me anything I don't already have. But, then there is that little voice in my head that says . . . "for now." And, then the FOMO kicks in. What if I regret not jumping on this while the opportunity is here? CCV has a fantastic points chart. It's the last of the O14 and, thus, has the longest contract life. The theming is incredible. The more I think back to my recent stay, the more I am remembering just how great the theming was. I think I do look forward to sharing the resort with my family for years to come.
But, all of that can be accomplished with resale CCV. I don't have to have direct CCV points for that. Then, I wander over to
dvcforless.com, and see how much it would be to pick up some more resale points if I wanted to. I see the listings, look at the CAF, think about the haggling and resale process, and think, for about $10,000 more (per 150 points), I can just call my guide up this Saturday and, boom, it's done. No, $10,000 isn't nothing, but the contract has 42 years left on it - it's not so much when spread out over all those years.
Of course, I also give a little bit of a thought to the fact that "sold-out" pricing of CCV is $155. This incentive with this sale is $24/point. So, I suppose if I end up regretting passing this up, that's about $3,600 (per 150 points) more to purchase at full "sold-out" pricing. TBH, if I take the extra cash I'd be spending to get direct, just keep it invested, that amount of money can be made pretty quickly - OTOH, DVD will likely raise that "sold-out" price at some point, and that means less years of use out of those points, so then I'm back to the notion that the cheapest time to buy, if I want to do it, is today.
I also think, well, if I end up regretting buying more direct points, what would be the best way to hedge. Maybe only buy 150 points during this flash sale instead of the 300 I was initially thinking. Or, maybe break the points up into smaller contracts for ease of resale. If I get 150, should I do 3x50, 2x75, or 1x100 and 1x50? If I get 300, should I do 2x150, 4x75, or 2x100 and 2x50? Then I'm over on the site sponsor looking at their opinions of value on the differing sizes of contracts, but who knows whether that trend will be true 10-20 years from now. So, why spend the extra money to break up the points for some theoretical potential future value. Just don't buy a single 300 point contract, and it's probably fine.
Ok, thanks for reading my mental mind dump. I welcome any thoughts, advice, or words of wisdom. Can't promise I'll listen, but I really appreciate hearing other people's thoughts.