You know if we want a bit flexibility when planning your travel needs, I would suggest getting credit cards that offer points/miles independent of any loyalty programs, at least initially. Like you I don't mind paying for some of my travel expenses, so what I have done is used a combination of points/miles and money to pay for some my trips. I have use my Chase Sapphire, CitiBank ThankYou, Capital One, and AMEX points and miles to "subsidize" my travel expenses. In the long run you may end up accummulating loyalty points and miles with any hotel or airline chains and even status, but you can still have the flexibility to use your credit card points to pay for part or all of the trip anytime you want to go, not just when a airline or hotel opens up award space. It is good way to stretch your points/miles and be able to take more trips (and even fly in C or F depending where you want to go). Last year I traveled to Europe and used LH miles I had accumulated through flying with United to upgrade to C (one-way outbound). I used my Cap One CC to pay for two upgradeable tickets and afterwards I partially reimbursed myself through Cap One's rewards program. In all, I paid about $1500 for the RT (C class out, Y class in). And I even got some of the miles back from LH for flying.