Well maybe you spoke to vicious or something. But ignore him, he has no life (and how do you kill that which has no life?).

I've been playing for a very long time now and 'only' retired 6 times. I also have a few alts, which i've never retired. Some of my clanmates have retired dozens of times.
I've had a long period pre-patch where i decided not to retire anymore, because the generation xp bonus by itself just wasn't appealing for me. That, and i was just getting started with the tactics and flags, so my higher level (i think i was 42 or 43 or something) helped me survive all the attention i got carrying that red flag around trying to lead the troops.
I might retire again and maybe improve my shield a bit or something. Or maybe i'll spend some more time on my alts.
I can understand that with three level 29 characters, heirlooming doesn't seem appealing yet. That's fine! But i bet after a few more months of playing, that you might just consider retiring again a few times. But don't feel like you have to!
The great thing about the heirlooming system is: you don't need to retire. If you want to and enjoy the challenge of having a lowbie character once every few weeks, heirlooming is great. I've tried almost every build i wanted to try. I've heirloomed my horse three times (which i do admit really does seem worth it) and i've heirloomed my weapon three times. So i'm happy.
What i like about the heirloom system is this: you don't
need to retire, but it does give you something to strife for if you've been playing for a very long time.
Don't get fooled into thinking you need heirlooms. You don't. But get them if you enjoy a challenge and don't mind being 'weak' again for a bit. And don't get caught up in the 'i must heirloom every item i use' crazyness, unless you enjoy that kinda thing. It's a LOT of grinding. Don't do it for the advantage. Do it because you want the variation. Or limit your heirlooming goals to something realistic and healthy.
Eventually, you might just heirloom every item you use. Or you might not. But don't feel like you need heirlooms to win, because really... you don't. Teamplay > gear. And skills > gear.
Instead, if you feel the game is becoming boring, try leading the troops. Do some tactics. Spend some time lugging those flags around and making plans with your teammates. It will entertain you for many more months, i bet. It works for me.

P.s.: the one thing i dislike about heirlooming is this: it does kinda make you use the same heirloomed items a lot. The effect is more psychological than rational, but somehow using a unheirloomed sword loses it's appeal now that i have my masterwork scimitar. Which is too bad, because i did enjoy searching for the right sword. I still have a dozen swords in my inventory, but never use them anymore.
Edit: P.P.S: however, i really do enjoy looting heirloomed weapons on the battlefield. Sometimes, when i'm on foot, i pick up a masterwork side sword. That's fun. Or i get lucky and find a champion sarranid horse. That's exiting. I even tend to pick up stuff like a masterwork flamberge or a masterwork pike, even though i'm not proficient in two handers or polearms on that caracter. So looting heirlooms on the battlefield is awesome. I even hunt certain players (sorry kingrimm

) because i know they carry items i want (like his heirloomed huscarl shield).