Have you date-checked your brake hoses? Remember, if they are ten years old, or have 100,000 miles on them (whichever comes first) they need replacement. Replacing a couple of brake hoses sure is easier than doing the bearings!

I haven't, but thanks for the suggestion, as I had no idea they even had a date code. Might as well do that whenever I rebuild the calipers, and the fluid will get changed later this year anyway.

I think the bearing is going to have to get done eventually no matter what - I'm not even certain I have a sticking caliper - the wheel has significantly more drag when I turn it by hand than the other side, and every once in a while I've had a slight pull during braking, but I don't seem to be getting more heat (or brake dust) at that wheel.

Use a power bleeder, you need to completely change brake fluid, change your hoses.

figure it out today:

Wheel bearing is fine - the play in the wheel is from the upper strut mount. Another older thread I found this morning made me think to check by sticking a finger in between the strut housing and the cover, and I could feel the play there. Good news for me, as it's easy to replace and not critical, so it won't keep me from taking the car.

Squeaking is definitely from the brake (I did notice today that it goes away when I press the pedal). I do have a slightly dragging caliper. Already have a new seal kit for it, but I checked the hose per suggestion and it is old, so I will order new flexible hoses and probably the hard lines at the caliper too just in case and do a front brake service next month.

Thanks for the help!