I actually did catch the fraud before the statement closed (around a week before closing), but Chase still counted the spending against the $2000 limit. I thought that was very odd as well, and when I called Chase to dispute, since it seemed like this should be on them to fix, they told me there was nothing they could do since the points had already been allocated to my SW account. That sort of fits my experience with Chase customer service in general though; have never been very thrilled with them.

No hotel points other than the Marriott points I have leftover from last year's travel, as I've been doing RocketMiles for all my other hotel bookings this year to get SW / AA points.

One thought I had: with Christmas spending, I can get my needed points down to around 24K. If I were to purchase 50K Marriott points, a buddy of mine is willing to purchase 5K Marriott points on his account on my behalf and gift them to my Marriott account. That gets me to 70K Marriott points total, which I could convert to 25K SW points for an outlay of less than $700.

Based on the forum's experience, anyone see an issue with timing to get the points into my SW account by Dec 31 if I do all my Christmas shopping before my statement closes next week, purchase the Marriott points (and have my friend purchase the gift of Marriott points on my behalf) today and then transfer them to SW RR points immediately as soon as they're in my account?

Edit: to address your point about the other two cards, I've only had the one. My only concern is throwing away the 50K points toward CP that this one got me right now. I definitely plan to get the other two cards late next year, provided I can get the CP for 2016 by Dec 31 of this year, and using them early 2017 to get a 2017 / 2018 CP.