One mate likes to check luggage; the other doesn't

My significant other and I are getting ready for an overseas trip that requires plane and airline changes.

I will only check a bag if I absolutely have to, because (1) I need what I have in there and don't want to wait hours or days to get my things; (2) I hate waiting at the airport to check bags or to retrieve them after arrival (and worry when everyone else's turns up on the carousel, and mine is last); plus, (3) I resent paying fees for checking bags.

My SO is of the opposite mind. He hates lugging or rolling bags through airport security and to the gate and fighting for scarce overhead bin space. He'd rather be unencumbered as long as he can. Even though his bags have been delayed in the past, he'll take the chance.

This trip, we're not staying near the airport where we eventually land and will need gear for hiking. I told him it's risky to bet our bags will make the connecting flight and arrive with us. He's willing to take that risk.

So I'm carrying on (and will sneak some of his important stuff into my roll-aboard), and he isn't.

We'd like to know what other couples do in this situation: Do you yield to the checker? Take turns carrying on or checking? Always check? I realize this may not be an issue on short trips. And I also think we all tend to pack more than we need, and carrying on encourages paring down. Next trip, see what was unworn when you return home.

Thoughts?