Re: When to give in and sell? REP given
Looking at your team, I don't see too many "sell the farm" pieces other than Giroux. Normally when teams kick start their rebuild, they sell off their older stars. But your older stars are Crosby and Ovi and in my experience, they will be way more productive for a few more years than anything you receive from trading them. Basically they are elite players but typically don't garner that value in trades due to their age.
I would try and improve your goaltending position. Having the SJ tandem must have also hurt this year (coming from a Sharks fan here).
12 team dynasty, weekly H2H, daily starts
3C, 3LW, 3RW, 4D, 1UTL, 2G, 7 Bench - 23 player roster, unlimited farm system
Cats - G, A, PTS, +/-, PIMS, PPP, SHP, Hits, SOG, BS, W, GAA, S%, S and SO
C - Crosby, MacKinnion, Bergeron, Kopitar and Pageau
LW - Marchand, Pacioretty, Nugent-Hopkins (C) and Vrana
RW - Stone, Voracek, Duclair (LW), T. Wilson and Tanev (LW)
D - Hedman, Doughty, Trouba, Weber and Giordano
G - Holtby, Binnington, Quick and M. Koskinen
Farm
Highlights - Cernak, V. Soderstrom, T. Harley, V. Heinola, R. Andersson, C. Garland, C. Grundstrom, P. Kochetkov
Picks - 2020 1st, 2nd, 4th and 5th