I have a Travelpro Platinum 3(?) 22" expandable rollaboard suiter. One of my very first trips with it was for 5 days, so it was stuffed pretty full. To my dismay, it did not fit in the overhad bin on an MD-80 on the way home.

I went through much the same thought process as the OP -- oh no, my brand-new suitcase won't work in the overhead bins! What I learned is that it's possible to pack it full enough so it doesn't fit, even when unexpanded, but it's also possible to pack it so it fits fairly easily. I just make sure not to pack it to capacity anymore.

A year and a half later, I've only had one other situation where it hasn't fit, and that was in the middle section of a UA 767. It consistently fits wheels first into the overheads on an MD-80.

And yes, heads-first does sometimes work better. A FA showed my husband that trick a few months ago, and now he always does that.