I'm not terribly experienced with this, but I'd imagine that the success of anamorphic over letterbox (when using LD as a source) would depend heavily on filters, programs, techincal knowledge of what you're doing, etc. Because honestly, the difference isn't that big. I agree completely when it is said that anamorphic usually looks better on a widescreen TV because the computer has done the hard work (rather than the decoder). You can get some nasty stuff when you merely press the zoom button on a letterboxed DVD (with a widescreen monitor).

I'd probably go anamorphic, but I'd need to do a lot of reading to get up on all of this. All of you have done the hard work already!