Alright. 3 pairs of <$100 cans in, I can come to some conclusions and hopefully help anyone looking for an entry level pair. In my case, I do my critical listening on speakers. The cans are just for my desktop pc and android phone.
So:
Sennheiser HD428
I bought these at Best Buy for $80 without really doing any research. I just knew Sennheiser was a trusted brand, so I gave them a shot. While they do their job, they are the most boring headphones I own. Nothing stands out. Everything is slightly veiled. Just a really boring sound. The $30 Skullcandy IEMs I bought with my PSP blow these out of the water.
It's one of the cases of nothing being wrong, and nothing being right.
-so-
I bought a pair of headphones suggested in the OP
Superlux HD681
These are AKG 240 clones. The sound is a lot punchier than the 428s, and the bass get's quite a big lower. I'm really happy about the sound I get from these, but the clamping, oh my god the clamping. Don't buy these cans if you've got a big dome. I wear a size 8 fitted, and I couldn't keep these on for more than 10 minutes at time. It's a shame because I love the frame and leather band construction. I just wish the metal frame was a little more forgiving. Maybe I can leave them on something to stretch them out?
These are an absolute STEAL at $35 and are the most well rounded of the three I'm writing up. But I wouldn't recommend them to anyone with a hat size bigger than 7-1/4.
-so-
I bought the cans I almost bought when I tried the Superlux
Sony XB500
Coming from the speaker world, Sony is bascially synonymous with crap. But these are great! Comfortable as hell. Very light without feeling fragile in any way, and the bass. Zomg the bass. If you're a bass head like me, there is simply no other way to go. These things beat. I love the flat cable too. Only had these for a couple hours but man, I'm really impressed. Picked them up for $38 from Amazon factory refurbished. If anyone is wondering, I have quite a bit of experience with refurbished gear. My first engineering job was a Clarion refurb center and later at a Pioneer production center. Let me tell you, the quality control at the refurb center was much much stricter than the production center. So I've been a big fan of refurbs ever since. Almost all my stereo gear is refurbished, and now my headphones are too.
They came packaged in a generic white box with a Sony label with serial no. etc. and some Sony logos. Everything inside had a hand initial sticker sealing the bags. Needless to say, everything performs exactly as it should.
I'm EQ-ing a little bit to brings the highs out. The sound isn't for everyone. There's a very pronounced V sound signature, but that's exactly what I wanted. After spending thousands of dollars on home audio gear, I've come to hate the sterile monitor sound. Even if it is a more truthful representation of the music. Buy hey, this is coming from a guy who got his Kuro ISF Calibrated and still use my own uber contrast setting.
Thanks HiResDes, Dreams_Visions and everyone else who helped my learn about quality headphones. These XB500s are e.x.a.c.t.l.y. what I was looking for.