OK this is kind of my game. I travel all the time and have barely paid for more than half a flight in half a decade and have stayed at some pretty sweet places on the house. I've scaled back on my CC shenanigans as of late because #### flying with two small kids but here's the rundown anyway.
General strategy: Acquire Chase Ultimate Rewards points, and pair them with a Chase card that grants you access to the premium transfers. Want to fly to the orient in a private suite with a bed for no money out of pocket? It's either this or AMEX Membership Rewards points that are going to do that for you and AMEX cards have high annual fees and most earn like #### beyond the sign-up bonus. People get giggity over earning 1c or 2c per point but with the right transfers you can get 10c - 40c per point out of these. And you're much better off stockpiling your points all in one place to be transferred out in bulk rather than having a few points here and a few points there in all the different rewards programs. That's not even to mention the flexibility of being tied to one rewards program for years and then watching it turn to #### after you've built up a ton of points like may happen here shortly to Starwood folks. Lastly, it means you can combine sign-up bonuses if you need to build up points quickly since there are a ton of chase cards.
On that front, to do that I have:
Chase Freedom: No fee so no brainer with the 5x points in rotating categories. And rotating categories that you actually use, at that (restaurants, Amazon, gas, groceries, etc). The points on their own are crap, worth 1c each but that value shoots through the roof when paired with...
Chase Ink Bold (would also work with the Chase Sapphire): This is one of the premium fee Chase cards that gets you access to the premium transfer partners (pretty much all the airlines that matter). The bonus in this is that you can transfer points between your UR (ultimate rewards) banks so you can transfer all your points from the Freedom account into your Ink Bold UR account and bammo, now all those 5x points you've been earning with the Freedom are worth a ton instead of being just redeemable for ####ty cash at 1c each. Plus your Ink Bold earns 2x points on utilities, etc so put all of those on auto-pay and forget about it.
Chase Hyatt Card: Remember when I talked about flexibility above? This is one of the reasons why. UR points transfer to Hyatt at 1:1, but Hyatt redemptions are quite cheap compared to other hotel chains. Their HIGHEST redemption category is 30,000 points/night. That means their top of the line, best $1000+/night hotels redeem for only 30,000 points, transferable from your UR account where you're earning 2x-5x points on many of your purchases. This is the dream, people. By focusing on point transfers you're able to combine the cheapest hotel redemptions with the fastest points earnings. So all told you can rack up enough points to stay a night at a freaking category 1000 Hyatt on the beach in Kauai after just $15,000 - $20,000 in spending (roughly 1 weeks worth of spending for a FBG). Having the credit card here just gets you a few extra perks while you're staying there, earns you a few extra points on your purchases while staying there (because let's face it FBG's are dropping $300+ at the hotel bar and golf course daily) and as a bonus it comes with 2 free nights at any Hyatt hotel. Yes, again, any hotel. Times Square, Paris, whatever. You also get 1 free night at a cat 1-4 annually.
AMEX Business Platinum: Don't necessarily have to have a real business. This is one of the cards with bigtime travel perks. First class lounges at the airport, elite status at the rental car companies, etc. It comes with a hefty price tag at $450/yr, but for one year you can easily make that up. Firstly it comes with a $200/year credit at an airline of your choice. Technically for incidentals (baggage fees, wi-fi, drinks, etc) but for some airlines you can use it on gift cards that you use to make ticket purchases (I used Delta). The trick is that the credit is once per CALENDAR year. So if you sign up for the card in August you can redeem for $200 then and then redeem again in January for another $200. On top of that you get a $100 credit back if you sign up for global entry, so at this point you're at +$50 in your pocket not even counting all the elite perks. Additionally, if you get targeted for it you can get offers of 100k up to 150k Membership Rewards points on sign-up which are in the same category as Chase Ultimate Rewards for buying power.
Chase Southwest Preferred and Southwest Preferred Business: Simply put, these are here to get you a SW companion pass, which means if you buy a ticket on SW your spouse gets a ticket for free (BOGO!). Basically when you accrue 110,000 rapid rewards points in a year you get a companion pass for the rest of that year and all of next year. Each of these two SW credit cards (again, you don't need a real business) has a 50,000 RR point sign-up bonus. So by the time you spend 10k you're at the companion pass. You've now got 110k points to spend on tickets and each of those ticket purchases comes with a free ticket for your wife. Good luck using those up so you have to pay for a flight again before your companion pass expires, which if you time it right can be 2 years away (get your 100k credit in January and then you'll have your pass for all of the 11 months left in that year plus the next full year).
So at this point where are we? WIth a year's worth of spending you're now flying to New York by using 25k of your 110k Rapid Rewards points for your ticket. Your wife's ticket is free thanks to your companion pass. You arrive at the airport and head to the first class lounge thanks to your business platinum card. If you need a car rental when you arrive you skip the counter and go straight to the executive area where you take your pick of premium class cars. Then you head to the Park Hyatt New York hotel with average daily rates of $800/night, but F that noise you're staying on the house for 5 nights courtesy of the two free nights from your Hyatt card paired with a mere 90k points out of your UR account that you built up in no time thanks to just one sign-up bonus and some smartly strategized card usage to manage your plethora of bonus earnings categories. And when you get home you've still got enough RR points for like 3 more domestic flights for you and the wife and probably a nice bucket of UR and MR points still sitting there as well either for another hotel or if you want to fly something like Emirates or Singapore Airlines (where the really lucrative rewards redemptions are) overseas.
I have a bunch of other cards too for various sign-up bonuses and bonus categories but my fingers are tired now so I'm going to go ice them.