Worst Websites of the Year
Worst Websites of the Year: 2012-2005
Daily Dose of Bad Design (Daily Sucker)
Current Examples of Bad Web Design Presented Daily (direct link)
Bad Web Design
Overview (direct link)
Worst Websites of the Year: 2012-2005
Current Examples of Bad Web Design Presented Daily (direct link)
Overview (direct link)

Checklist 1 | Checklist 2 | What do I do now? | The Top 30 Web Design Mistakes
You have to be born into the Roman Catholic church to truly appreciate the first question -- pre-Vatican II Catholics will understand it best. Back in eighth grade one of my male classmates at St. Andrew's School asked, in all seriousness, the above question. The question has stayed with me for forty years. The answer escapes me.
Non-Catholics will still appreciate the question. Basically, it's the same question they ask Google's Matt Cutts (except they don't phrase it as honestly): "How many stupid tricks can I pull trying to get my site to the top of Google's rankings before you punish my site?"
The mistakes in Checklist 1 are fatal. I'm not sure how many of the mistakes in Checklist 2 you can make before you kill your web site.
One of the areas I skipped is Search Engine Optimization and web design — mostly because many factors aren't design related. One of the best sites for all things search related is WebmasterWorld and a good friend of mind informed me they recently had an incredibly fascinating discussion entitled "25 Signals of Crap."
While many items mentioned are found on my two checklists, they frame them in the context of Google and advertising. You really need to read this forum discussion.
Checklist 1 | Checklist 2 | What do I do now?