I think I get where you're coming from, Gally. I founded a local Contract Dynasty League that is entering it's 20th Season this year. For several years now, I, and others, have tossed around the idea of bringing this League to a close, and starting over from scratch.
Way back in 2000-2001, Dynasty Leagues were just becoming a thing. The co-Founder and I had been invited be part of an online startup the year before, and had enjoyed it so much, we decided to bring the format local. We each played in several local season-long and keeper Leagues, and there were plenty of other buddies that were in one or more of them (all bar/restaurant people), and we hand-selected a 'best of the best' 14 Owners from about a half-dozen Leagues to be part of our initial Disbursal Auction, guys who we felt had the passion to make this thing work for an extended period of time.
While some of these guys had been playing FF of some sort all the way back to the late 80's, early 90's, most of it was pretty simplistic. Things like performance /yardage scoring, flex and ppr were nascent. Contract/Contract Cap? Yeah, right. Huh? There was only one Auction League, so only the guys who were members of that League had prior Auction experience, and across 14 Owners, our sum total of Dynasty experience was the one year each that the co-founder and I had had running our Teams in that online startup. Most of them were playing by the seat of their pants, figuring it out as they went along, but we selected well. There were a few defections after year one, but we still have 7 Original Owners + 2 that have been there since Year 2. Man, have we come a long way since.
Here's a prime example: for the initial Player Disbursal Auction, every Owner had $1000 Fantasy Bucks to spend. The catch was, whatever you didn't spend in the auction became a tradeable asset whose primary purpose was to spend in the subsequent Season's RFA Auction, in addition to a small yearly disbursal, and those accounts rolled over yearly. Most of the guys spent like there was no tomorrow, but some were wiser, and a few were quite frugal. It didn't take more than a few Seasons for everyone to figure out that Fantasy Cash is King in this League, and he who has the gold, rules. Almost all the consistently successful Teams from about Year 4 - Year 12 were those who were either wise or lucky enough to come out of that initial Auction with lots of FB, and figured out the value of those FB increased over time. That's the most common complaint - wouldn't have spent like a drunken sailor, if I knew the ramifications down the road. Now, 19 full Seasons under our belts, there's been plenty of time to correct that, provided that one has the discipline to build a cash reserve, but there are guys who'd love a fresh start with the trove of knowledge they've compiled over almost 2 decades.
We've come a long, long way since then, and every year a few voices pipe up regarding what it would be like to start from scratch had we all known then what we know now. I might personally take a different tactic - I wasn't sure it would survive, and if so, for how long, so I played 'win now' out of the gate, won the first year, placed a heavy emphasis on 'the future is now' for the 1st few years, and then couldn't bring myself to go into a rebuild for several years, and remained mediocre for much longer than I should have, before biting the bullet.
I don't know how you could pull this thing off without giving people a window of a Season or 2, to tie up loose ends - you know, revise strategies with a longer event horizon to account for the end date. Otherwise, I think a lot of Owners would be upset. Especially playing for a boatload of $$$, like we do.
This could turn into a great discussion. Looking forward to seeing how it plays out.