UM Pro 30 (1st Generation)

Shure 215 is the best value option. It's generally good enough for singers and instrumentalists, and can be made to work with bass if you mix it right. Shure 315 adds another driver, but also adds a bit of cost. If you want a little more ooomph on the low end, I roll with Westone UM30 -- but any two or three driver IEM will have much better and clearer bass response than a single driver.

I have a Behringer P2 wired pack and Westone UM30 for ears. UM30 monitors are a \_huge boost\_ over basic Shure 215. My P2 works quite well, considering how hilariously bent out of shape the metal is. P2 should run $40 or so. I think I bought my UM30 on sale for somewhere between $200-$300. Very rarely do I play a stage where I would greatly benefit from a full wireless rig, but I've often thought about upgrading.

Westones. They have a selection of responses to suit your needs. I have the 3 driver ones for extended bass, I'm a bass player and bg vox. Good isolation, good clear reproduction. Comfortable to wear for extended periods.

I have the foam ones from Westone I got a few years back. Triple drivers and they sound amazing and were very inexpensive. I got them used off Marketplace. I’m a drummer/singer and I’m moving a lot and they never ever once tried to fall out.