I agree Kink. I don't think any of Brawl's faults were made to be intentionally bad, but intentionally good... although I don't quite get tripping. Tripping as a result of an attack or getting hit makes sense, and definitely makes sense, whereas random tripping... is just stupid. Making players "trip" while make a sharp turn, trying to dash dance, etc makes sense (although it's stupid sense), whereas random tripping with no pattern is just absolutely ridiculous. It's like that one negative thing you always "fear" happening while playing. Things could be going good... until you trip into an attack. Once such a thing happens to you in a match, you "fear" it. Maybe "fear" isn't the most precise word, but still, I think you get what I am trying to convey.
As for the design, I blame Satoura Iwata for getting Game Arts, and HAL Laboratories for being busy for like 7 years making 3 freaking Kirby games (although they turned out rather great). Game Arts, quite frankly, is not a company that can make competent fighting or platformer games; they can only make decent RPGs well.
Monolith Soft (another Brawl developer) had minimal experience with fighting and platformer games (although they can make great RPGs). Paon (the third Brawl developer) at least can make somewhat good platformers. Even still, only part of the staff at both of those companies helped develop Brawl.
You go back to Smash 64 and Melee, and you constantly see how much HAL Laboratories pushed smash bros forward. You flip up to Brawl, and the only additions were "basic." A story mode, online, stickers, and stage builder. All of these features were "generic," and felt like they had minimal effort. Heck, even modes like Break the Targets and Event Matches were shorter and had "less to do" than Melee. Heck, I'll take Smash 64's 12 character specific Break the Targets stages over Brawl 5 generic Break the Targets stages any day.
Really, that's why I go back to Game Arts failing. Sakurai clearly was as motivated as ever. He added great new characters, had a load of ideas for a story mode, online, graphical design, stage choices, music, and stage builder. However, most of it fell flat on its' face (like how the graphics for characters make them look like "cut outs;" however, the music was successfully amazing!), due to Game Arts being rookies at this (Sakurai and a few other people actually had to train the staff for a few months), Nintendo's heads poorly organizing the Brawl project, and the Wii being just a slightly stronger GameCube with motion controls.
With Smash WiiU and 3DS, we got 2 strong consoles. The 3DS has way more memory than the GameCube, DS, or Wii, and the graphics aren't too far behind the GameCube. With Smash WiiU, we got a console that makes the PS3 and Xbox 360 look weak with huge graphical and processing power. Heck, I wouldn't be surprised if the WiiU had 10 times the graphical or processing power of the Wii or GameCube. Plus, these consoles actually support DLC, modern technology, have modern online, and aren't "a blast from the past."