When does a rebuild end? [General strategy question] (1 Viewer)

I've seen a LOT of discussion (both here and on other sites) about how to figure out if it's time to throw in the towel and start a rebuild. There's also a lot of information about how to rebuild. But I've never seen anything about the reverse -- how do you know when your rebuild is "done" and you should change your mindset back into contention mode?

I'm new to dynasty and have never done this before, but I assume there's a clear moment when you "pull the trigger" to end your rebuild and start acting like a contender again. Is this how you've done it in the past? If so, what signals do you look for to know that it's time? Are you proactive about it, or do you wait and tank until your team is too good to tank successfully?

Or am I wrong, and there isn't a single moment when you flip the switch? Does anybody just let momentum carry them from "actively making aggressive rebuilding trades" to "accepting rebuilding trades when the opportunity arises" to "wait, my team is pretty good, let me start buying"?

[Trying to keep this conversation as general as possible, but more context on my team below in case the specifics make it easier to give examples/advice.]

I'm in a first-year dynasty league and I went with the Productive Struggle strategy -- I was ok losing this year, and spent the startup draft only acquiring players whose value were likely to increase (AKA ignore RBs and ignore anybody over ~30). I now have a core of QB/WR/TE that I am quite happy with, but some serious holes in my roster at RB/Flex/depth. I managed to flip some assets for 2022 draft picks. Originally my plan was to flip my 2022 picks once their value peaked and try to load up on 2023 picks. But now I'm worried about being in "forever rebuild" mode and wonder if it might be smarter to spend my draft picks, try to hit on a couple difference-makers, and try to fill those holes and contend in 2022. Any thoughts would be appreciated!

My team (Sleeper league, 12-team, 30-man rosters, SuperFlex, non-PPR, starting lineup: 1QB + 2RB + 3WR + 1TE + 1Flex + 1SF)

QB: Dak Prescott, Joe Burrow, Carson Wentz, Mac Jones, Tua Tagovailoa

RB: Tony Pollard, Jamaal Williams, Devin Singletary, Ty Johnson, DOnta Foreman

WR: CeeDee Lamb, Tee Higgins, Marquez Callaway, Marquez Valdes-Scantling, Gabriel Davis, Joshua Palmer, Quez Watkins

TE: TJ Hockenson, Pat Freiermuth, Cole Kmet

2022 Draft Picks: 1.01, 1.02, 1.06, 2.01

I would say if you are doing it right you are always "rebuilding" and "contending" at the same time.  The owners that go full rebuild tend to always play for next year and next year never comes.  The teams that have had the best success in all my years of playing are the ones that are always competing and then making moves to get younger continuously while still trying to win.  They are never playing for next year.  Too many things change (injury, coaching change, free agency, draft, etc) to really know that next year is the year.  By always trying to compete while having an eye for younger improvement you are never playing for next year.  

As for your team I would try and trade at least one QB.  You don't need 5 that are all basically in their prime even in SF.  3 or 4 is ideal depending on who they are.  You have a nice stable so I would look to trade them to improve your RB's.  That is the first step I would look to do.  You are also in need of a stabilizing veteran WR for your WR3.  I might also keep the 1.02 (unless there is a guy that you value way over every other draft choice that you need the 1.01) and trade the 1.01 and/0r 1.06 for known commodities that can help you over the next couple of years.  This brings me to my other suggestion.......look at it over 2 year increments.  Any longer than that and you put yourself at a disadvantage.  As I said earlier, too many things change to worry about anything beyond next year when evaluating moves.  

Hope this helps.