For me I was able to extract value with maybe... 5-6 trips a year minimum. More then that and it just gets easier. But I guess it partly depends on what you're valuing.
For instance... If you travel with no checked bags ever, and you fly on an airline that requires you to pay for checked bags. You won't see the value of having free checked bags when you achieve an airline status. There's lots of little things like this.
I didn't care about checked bags. If I have to jump through a bunch of hoops to get a limited (and expiring) $200 credit it mostly annoys me more than helps.
For instance... If you travel with no checked bags ever, and you fly on an airline that requires you to pay for checked bags. You won't see the value of having free checked bags when you achieve an airline status. There's lots of little things like this.