Taking damage has always been something that makes Connor human to write and also human to read, because he's not invincible and has both mental and physical scars that act as both a harsh reminder but strong motivator. Off the top of my head....
[member="Taeli Raaf"], in her time as Sith Darth Arcanix, cooked his back with Force Lightning and left a nice tapestry there. He also has scars on his knuckles from when he experimented with Force Lighting himself the first time - it's not something I imagine you just throw about without seriously hurting yourself
[member="Keira Ticon"] has broken his ribs and given a fair few bruises and bloodied cuts which he always pretty much asked for
[member="Matsu Xiangu"] has given him most battle scars of all types - from embedding Sith Magic in his brain stem which left him very volatile and open to nightmarish visions when his emotion flared up (thankfully exorcised now!), to a nasty confrontation that left the right side of his torso riddled with little indented scars from falling across stones that embedded in his skin, to a skin laceration on his right wrist in the same fight. She's such a doll.
So yeah, I enjoy making him bleed when I have to - as I say, if he's attacked, he will hurt unless he is stronger and can avoid it by skill alone.