1. I think of this as time well spent compared to the time I waste when I've gone off track from GTD. Make sure it's uninterrupted time. I sometime leave the wife and kids at home early in the morning and go to a quiet coffee shop to get it done.
2. If it's been on your list that long, then's it probably something you want to do but have not committed to doing. As a result, it's probably a someday/maybe.