The question is simple really, when is it time to finally pull the plug on a browser version and just not care about supporting it any more? As can probably be expected this is in regards to IE6 specifically right now. A site I'm working on right now has a mostly-finished design that needs to be integrated but most of the back-end functionality isn't expected to be done for another 6 or 7 months. Is it really worth fighting with IE6 as apposed to just skipping it and supporting IE7+ instead? Also, the site in question is targeted specifically at photographers, many of which I know for a fact are mac-heads.
There's no magic answer to this question of course, though like the question the answer is simple. :)
You need to look at the data for visitors on that specific site, and then make a cost vs. benefit analysis, based on the extra effort it will take to support that browser vs. the number of visitors you expect to be using it.
There are other things you can do to make your life easier however. For example:
Your still supporting the browser in these cases, just not giving it the level of support that you might a modern standards compliant browser.
See Yahoo's Graded Browser Support policy.
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