Worst:
Fruity Loops 3 "Lifetime" upgrades - They changed the name to Fruity "Studio" so they would not have to honor the "lifetime" upgrades.
JVC XU-301 CD/minidisk player - I still use it but, I just don't like the way it works.
Sony MDS-JE510 Only worked for 1 year had a 1 yr warrantee.
EV ND767 wireless. - The mikes are great, but the receiver pops really bad when you switch them off and on.
Chicken System Translator - early versions never translated stuff very well.
HP Color LaserJet 4500 - It worked ok for 1 year had 1 year warrantee. It was way too expensive to print as few pages as it has. Now it jams all the time, hard to print because you get 1 good sheet and then 1 that looks like and accordion

Sony TD8 DAT - Jammed up alot. Heads always needed lining up.
Tama drum throne (bicycle style) - Legs too narrow, always wants to dump over
Steinberg - The Grand, Free filter, HaLion (dongle version)
Kinetic (sorry cake)

Adaptec EZ Cd Creator
All those cards for my Lexicon PCM-80
Not as good as I thought it was:
Universal Audio M610 - Too much color, I still use for DI box. Might be I don't know what vocal mike sounds good with it???
Focusrite Octopre - it sounds great, but the fan in it is WAY loud!
Best:
Sonar 6 / Cakewalk forums, Samplitude, Vegas Video, BDF & Drumagog-BFD Version, Prosoniq - Time Factory, Finale 2007, Samplit with Kontakt 2, NI-B4, Harbal 2.3, GPO, Waves stuff(I hate it and I love it!), EZPlayer FREE, Toontrack-CAV, Kurzweil K2500, Yamaha Motif ES7, Yamaha WX5 w/ patchman's VL-70 chip, Gemeinhadt silver flute (pd $500), Millenna HV-3D, AKG 414TLII, Neuman KM-84's, Taylor 312-CE, On-Stage studio boom/stand, Digital Juice Video loops, Ultra USB/Firewire hard drive enclosuers.
These are just some things that come to mind.
Max Arwood
edit spelling again