There is no formula. Every situation is different. Ideally, if you do decide to rebuild it should be done fairly quickly. As far as I am concerned, the only reason to do so is if you lack top flight talent. Therefore, if you have elite talent you should not trade it unless you get elite talent in return. If you don't have it then you throw yourself into the tank until you draft some elite talent. Then spend the rest of the time building around the edges picking up undervalued players along the way.

Everyone wants to build a juggernaut that will win for a decade. It can be done but it probably only happens if you have a weak league and then once you've built that juggernaut the fun ends or the league ends. In a stronger league the best thing you can do is what ED advises and simply never rebuild and the best way to do that is to avoid underselling assets.

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My strategy has been to try to win my pool every year.

Most of the results are based on sheer luck so you might as well draft the best team you can every season and see where the chips fall.

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10 Team Limited Keeper (Keep 7) Points Only
SALARY CAP (Player Salaries) League
12 F 6 D 2 G

F: Giroux, Tavares, Seguin, Ryan, Pacioretty , Datsyuk, Zetterberg, Pavelski, Ribeiro, JVR, Roy, S Kostitsyn
D: OEL, A Larsson, Yandle, Josi, Hedman, Faulk
G: Quick, Price

The article Eric provided has good advice plus a few links to other valuable reports.

Since it looks like the majority of your group is still a few years away I would look at options to trade your older players while they still have good value. Thornton and Anderson primarily are the two that should get good interest followed by Goligoski and Kunitz. I would just put it out there to the league that those guys might be available in exchange for young talent to gauge the interest. If there are no decent offers at this point I would hold off on trading them until the next season is in play and a contender is looking to shore up his team.

It looks to me that you are in a spot that will require patience for a bit longer but with the youngsters you do have your team will be heading in a very positive direction.

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10 team full keeper: 4C/LW/RW,6D,2G,5BN

G,A,P,+/-,PIM,SOG,GWG,PPP,SHP,Hit,Blk,FOW
W,GAA,SV,SV%,SHO

C- Giroux,Hanzal,M.Richards,J.Staal
LW- Lupul,JVR,Tlusty,Zetterberg
RW- Backes,Clarkson,Havlat,Kessel
D- Bogosian,Carlson,Enstrom,Kulikov,Markov,Yandle
G- Miller,Hiller,Crawford
BN- Kuba,Ruutu,Robidas,McDonald

Prospects- Armia, Connolly, Couturier, Etem, Forsberg, Girgensons, Huberdeau, Kucherov, Nyquist, Okposo, K.Palmieri, Stransky, Toffoli, Barberio, Gardiner, Gormley, Josi, Marincin, Moore, Morrow, Savard, Vatanen, Allen, Bernier, Campbell, Fasth, Hackett, Mrazek

Even if a rebuild is done very successfully I still think if the same effort was put towards winning you can have a contender and win championships more quickly. People are more eager to trade in fantasy hockey and frankly some GMs are not very good. Don't get discouraged and stick to the plan of making the team better.

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UHL Calgary Flames
24-team H2H (roto G, A, GWG, SHP, PPP, PIM, +/, SOG, Hits, Blks, FOW, W, SV, SV%, GAA, SO)

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