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It's possible the one side on your headphones crapped out, actually. test them with something else, like your laptop.

SID bass does it for me.

I know the answer to #2 - you can use MSSIAH with a single sid, but you wont get 6 channels out of it, only 3.

YES YES A MILLION TIMES YES. THIS IS AMAZING.

It's easy. google image search "prosound mod" and look for the picture that shows where each wire goes.  Use that.

For real, my list so far:
cTrix
Knife City
Sievert
exileFaker
George and Jonathan
10k
Wizwars
Zen Albatross
4mat
Greenleaf
Doomcloud/Steady C/SadNES/Oxygenstar
Rhinostrich
Note!

and if guests from previous years are allowed....
Trash80
Mr. Spastic
IAYD
J. Arthur Keenes Band
Cheap Dinosaurs
Alex Mauer
David Sugar

Get the lsdj demo from the website, emulate it, and see if you like it. Do the same with the nanoloop rom. That way, before spending any cash on hardware, you can see if one piece of software better suits you than another.
Also, noisewaves is right - there's lots of ways to make chip on your computer without paying a cent.  Definitely check those out as well.
There's a myriad of ways to create chip music, it's all about finding out what works best for you. 
One thing to remember, though, especially in this community - people are helpful, but for the most part they love seeing that you've put the time in to look up things for yourself before coming to them.  The internet has all the information you need to make chip music, so make good use of it!
Best of luck to you.