I guess I can see it both ways: sometimes (most times), the hassle of checking a bag isn't worth it, but sometimes it's a hassle not to check a bag. I recently attended a 5-day conference and my bag was a daypack. My two colleagues, who had half-size roll-aboards, both had to gate check, and I admit I felt pretty good that I didn't (though ultimately it didn't matter since I had to go to the baggage claim with them anyway).
Later this month, though, I'll be doing a trip that involves formal occasions, including a wedding, and a lot of activities that require specialized garments or equipment; plus, my wife hates hand-carrying luggage. We have an REI Wheely Beast and we're checking that, and I don't care because it will make the overall experience more relaxed.
The only thing I really object to is when people over-pack their hand-carry luggage and then a) can't fit it in the overhead bin properly or b) drop it on my head when they're trying to wrassle it up there.