The first edition of this list was put together last year, and it is something I am going to update at least once each season. I have a few general rules when it comes to building a team in a fantasy hockey keeper league. One of the more important ones is to not plan beyond a two or three year window. You are not building a real NHL club, and too often I see poolies place too much of an emphasis on youth and prospects instead of trying to add players who could help them win now.
Using this rule, take a look at your team(s). Can you realistically say you will have a shot at winning the league at some point within the next two or three seasons? If not, time to scrap the rebuild and start adding proven NHL talent.