So the simple answer to your question is yes, purchasing 2 flights that each yield 5000+ points would put you over the hump. I would also ask how much value you plan on getting out of CP over the next 16 months (Sept '17-Dec '18). Some people get thousands of dollars of value out of it and would benefit from the extra, upfront spend of $1000, but if you only plan on getting $1000 worth of free flights then your plan doesn't make much sense. Since you also have 4 months of qualifying time remaining in the year, you could also continue to earn points through normal/necessary spend and Wanna Get Away fares/flights, reducing the extra spend required to get over the CP hump at the end of the year. If you only plan on getting $300 worth of free flights between now and December, but through normal spend you can reduce the point gap to the point where you only need to buy $500 worth of Business Select fares at the end of the year, then you've saved money overall ($200 in this example). Or if your planned companion travel isn't until later in the year, book flights for yourself now, continue your normal spend until closer to the companion travel date, and then upgrade a flight to get you over the hump, perhaps upgrading for only $400 instead of $1000, and then add your companion to the reservation.
Just a few thoughts, hope it helps you out. And just because I've seen way too many people get confused, make sure you're looking at your CP qualifying points in your account and not total RR points. CP points must be earned in one calendar year, January-December. I'd hate for you to spend a bunch of extra money thinking you were getting CP and then have you learn you didn't qualify.
