I'm playing a H2H monk, and was wondering if there's any way to add a cast-on-strike effect to my attack? (Something like damage endurance). Can I enchant gloves? Would a mod be required to achive this?

You need a mod. IIRC, there is a mod called fists of fire (something like that) that does just what you want.

Yes. http://planetelderscrolls.gamespy.com/View.php?view=Mods.Detail&id=1854