What card are you thinking of upgrading to if you don't mine me asking? Which actually is fairly relevant to the traveling thread when you think about it. I travel a decent (and increasingly less) amount for work using my own credit cards so earning points is a nice little hobby of mine which ends up paying for a decent amount of my personal travel.
I pretty much only use two credit cards. I have the chase sapphire card which gets me 2% back on hotels/airlines/rentals/restaurants which is great for my work travel (and personal use since I use it for everything just about). But the best part is when using their website to book travel, the points are worth 20% more. So $100 in points gets me $100 if I want it in cash, but if I book any travel it's worth $120. That really gets me the most bang for buck out of my points.
I have one other credit card that I've only been using for a year, but has really worked out well for me. That's my IHG Mastercard (also through Chase). Essentially I use this now only for my hotel bookings since for work we almost only stay at Holiday Inn Expresses. I have an insane amount of points with them that essentially gets me ~10 free rooms a year. But this credit card costs $50 a year and it also gives one free night (which I have set for South Beach on a Friday night $350 in value) so I say the cost is worth it.
Which leads me to my next trick in getting my free travel. Back to using those Chase points I earned for all my daily spending. If I burn those points booking airfare, I have found I still earn reward miles (I, sad to admit, use United). So I have about 100k United miles earned and I hardly ever pay for flights (that's work and my own free flights with Chase). Obviously I can only do this because work pays for me to travel about 40 days and 20k miles a year, but that's been my strategy to maximize it. My boss/coworker use Delta and use the Delta credit card to stack miles as their strategy. I personally just don't find airline miles worth much and like the flexibility with my Chase points plus the ability to earn miles using those points.
I haven't decided yet. Until I know I'm going to spend 4 grand in 3 months I'll just keep using an older card (still cancelling Aadvantage, though--it's annual fee time). The Sapphire card is definitely one of the 3 options. That's been the gold standard for a while now. Since I live in Dallas Southwest's card is a winner. Whole lotta perks with that one. Third option is just to get a cash back card.
Biggest problem for me is that I hate flying Southwest. Moreover, I never find it to be particularly convenient nor cheap. Unless you know six weeks in advance and can fly out at 0400 on a Wednesday morning it tends to be pretty pricey. I always travel over weekends so it doesn't work well for me. AA almost always does far better for me. Using SW's points works the same way. Maybe it costs you 5k, and maybe it costs you 19k, depending on the convenience of the flight. That said, their card gives you lots of free points and companion tickets on your anniversary, and they partner with a ton of hotels and rentals that score you beau-coup points.
Damn shame AA has gone the way it has. Since they hub out of DFW it's always been a steel for me. Now the points aren't worth a whole lot and they make them a PITA to use. Moreover, they've added a "Spirit Airlines" pricing tier that basically took up the original economy class, so now you pay the same price don't get to choose your seat and don't even get a free carry-on.
Really, frequent flyer programs don't work well for civvies anymore. Unless your company is sending you all hell over the place it's probably best just to find a good cash back card. My old man spent much of the 80's essentially being Clooney's character in Up in the Air, flying places to fire people and do their job until it's restaffed, and he's still spending the miles he accrued 30 years ago. Similarly, a dear friend (you met him down here at DT) makes a killing off of SWA. He travels 8-10 times a year with his old lady and is able to do the 000 Wed thing, so he's rolling in points. Someone like me that only travels 3 or 4 times a year over long weekends doesn't need to really worry about it all that much.