$300 is definitely not worth an extra 5000 points to me, but if that's the only remaining travel you have planned and that gets you to ALP, then it might be worth it.... There's no way around it, gotta fly for the ALP qualifying points.
To chase CP is much easier, as you get close to the end of the year, since it's much easier to get CP qualifying points, you can always just become a big spender, don't forget about Southwest Dining program, and if you stay in hotels or rent cars you can earn CP qualifying points too. Just remember that the points will need to post in the calendar year. If you go big spending in Dec. and your cc points post in January, then it will be all for naught.