I have a Traynor YCV40WR currently which I use for mostly reggae, ska, and a little punk.
Lately, however, I've become much more interested in playing stuff by Brand New, I Am The Avalanche, Say Anything, etc.
The sound is much heavier by comparison and I want to start a band that plays similar stuff, maybe with a little reggae and ska mixed in from time to time.

I don't think what I have now will get quite the tone I'm looking for, I haven't had much success so far.

What 30-50 watt tube amps will get me what I'm looking for?
What would you recommend doing with my traynor + pedals, mods, tubes to get what I'm after?
I want Super Saiyan abilities
Well, I see you have a DS-1. Maybe try just a strait up OD pedal like a Bad Monkey with and without the DS-1. If that doesn't do it then it may be time for a new amp. I'm not sure what your budget is and I'm not familiar with the bands you are moving toward, but these might be worth checking out.

No particular order, most recent to old posted over the past few days.

Line 6 Vetta $725

Laney Pro Tube 50 head $600 (needs cab)

Peavey Windsor 100w head $225 (needs cab)

Mesa 5:25 Express combo $895

Marshall JCM 900 combo $825 (yum)

It won't have anymore gain. I'm not personally experienced with the WR, but if it's similar to the YCV then you should be able to get some heavy tones by using an overdrive on the dirty channel. Hell try the ds1 as overdrive, just set the level high and the drive low.
I don't give a shit if you listen to me or not
that Vetta is pure sex at a nasty price, and you're guaranteed not to get any diseases.

I think, however, that you're trying to use a little too much gain for what you're playing. using a good distortion pedal would be ideal.
I'm putting my GAS on hold
for a couple months in order to pimp my ride.

Don't judge me.
i'm looking for better gain
not more
the dirty channel just isn't cutting it for me anymore
I want Super Saiyan abilities