I suggest deciding where you want to go and then deciding which hotels and which airlines. I'm chasing 1MM status with UA (which should happen by the end of the year), so I concentrate on hotels. I'm focused on Hilton, because citi is churnable (for the time being). I have gone to the Conrad Rangali Maldives for the last two years and will go again in Feb 2015. The basic room is $1000 a night, so I think the Hilton is worth it. I'm retired and travel a lot and skew my stays to Hilton, especially when there is a bonus. The Citi Hilton Reserve (and the Amex with the annual fee) both give gold status which I think is fantastic. Gold gives breakfast. When other hotels have great bonuses I've sprung for the card, using the points when it made sense. I spent almost all my SPG points on the Westin Excelsior Florence this month when the rooms were over 300 euro a night. (Now, I've got to figure out who to replenish my supply of SPG points). I've got points stashed away in AA, US and Delta, just in case. I used a bunch of Delta points to go to Fairbanks because I thought the fares were outrageous.

Figure out where you want to go. Take it slowly. It's better to dip you toes in slowly instead of jumping in over your head.

And the standard advice on FT holds--if you are not paying your balances in full at the end of the month, you shouldn't be churning.

With the Rangali stay (which is an outlier in terms of value per point), I save about $15k a year on travel through credit cards. That's really not an aspirational international vacation a year.

Read the hotel and airline threads to determine what programs make sense for you. Some people swear by SPG, but I still don't get it. I don't do business travel, so accumulating points by stays and spends doesn't go far with SPG compared with other programs.