I would prefer 2030 at the earliest for expansion. As for methodology - I liked 15 players from each team to get drafted. But would not limit it to one per team per round. If round 1 sees 15 players from team x taken then nobody else can be chosen from that team the rest of the draft.
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We wouldn't need to lose that many.
If each of the 20 existing clubs lost 15 players, that would be 75 per expansion franchise.
If each of the 20 existing clubs lost 10 players, that would be 50 per expansion franchise.
If each of the 20 existing clubs lost 8 players, that would be 40 per expansion franchise.
There is a sizable free agent pool at the moment that could be used to help fill the minor leagues.
One interesting thing you can do in OOTP that you couldn't do in 6.5 when the NPBL expanded is create the expansion teams a few years early.
So, for example, say the target is to add 4 teams in 2030....
In 2026, create the expansion clubs as unaffiliated minor league teams in a Rookie League. Let them participate in the draft (might be tricky, you'd most likely have to do this manually) and claim free agents.
In 2027, move those squads up a level to A-ball and create a R-league team for them to use. Promotions/Demotions would have to be handled manually by the commish since you cannot link squads as far as I know unless they share a parent major league club (and they wouldn't yet). They draft more players and claim more free agents.
In 2028 move them to AA. Now the organization has AA, A and R-league teams.
In 2029 move them to AAA. Now you have all levels except a big league squad.
In 2030, add the parent clubs... now the minor league teams can be officially linked in-game so Matt has to do less movement.
You could do a much shorter Expansion draft, because these teams would have 4 or 5 drafts under their belts as well as years of FA claims. All you'd need to do is get them 20-30 players, which could be done with each team only losing 4-6 players.