Of course I'm glad tattoos hurt: I agree it's an integral part of keeping them for the dedicated only... Willing to sit and take it for the lifetime reward of the tattoo.
But...
I got to admit that I stopped philosophising too earnestly about the educational or self improving nature of the pain the time I got my front lined out. It wasn't a relevatory experience for me ... I just felt like I got carved up! I guess I found my personal tipping point that day.
Small tattoos, or decent pieces most places on the body... I can grin and bear it and, yes, I probably learned a thing or two about managing pain mentally. Even my back piece was pretty Ok.
But a really long sessions on a sensitive place like the torso or ribs... mostly just makes me miserable end of story. Can't make a purse from a sow's ear.