When does analog compete with digital?

With vinyl becoming all the rage, many believe (perhaps mistakenly) that a budget of $1K will allow them to bring their analog front end up to par with their digital. I would like a reasoned assessment of this issue.

How much time, money, and expertise do you think is necessary before one can seriously claim that their analog front end can compete with their digital? What characteristics, if any, are simply incommensurable between these two mediums? Let's use my system as an example.

Personally, I tried to build an analog front-end that focused on texture/warmth (as opposed to dynamics), but I still feel as though something is missing. Trouble is, I can't quite put my finger on it. I'd be grateful for comments/suggestions (system in sig)