'99 2WD Dakota.
New pads, calipers, and rotors.

After driving a short distance (like something heats up), there's a grinding sound that comes from the front end...best I can tell from the drivers side but could be both?

You can barely put pressure on the brakes and it'll stop.

Otherwise it stops fine and no unusual noises when braking. The wheel bearings feel tight, and I don't really hear anything at highway speeds. I'm not sure if it's only happening in town or if other noises are drowning it out at higher speeds.

My guess is a pad laying funny / vibrating off the rotor, but cant swear on it.

I'm not seeing any abnormal wear marks anywhere either.

Any ideas what it may be and how to fix?

 

Look at the rotor splash guard it may be touching but why only curtain times is strange that usually means something is loose like a bad hub or splash guard.

A good check of a hub is pull a tire then the pads and caliper off now secure the rotor to the hub with a nut or two now pull push side to side up down hard any movement other than ball joints is bad. Next at a very quiet time spin the rotor and listen for grinding even small pops and ticks tell you its bad or going bad.

Get your ear as close to the spinning hub as possible securing the rotor to the hub will amplify any sounds coming from the hub.

 

Jack up front end and spin wheels by hand, to see if you can hear it.