Wow ! A lot of great ideas here. I recall some of my own wackier ones - I am grateful to bheid408 for bringing up one of the less impractical, even if his point about its potential weakness is well taken.
But I was probably premature in the days a few years ago when I was proposing a new prog concept every week. Now serious people are interested and so am I. contrarian23, whatever comes out of this discussion - and we are grateful to you for starting it - please let me know as I would join in a heartbeat.
So....what if we just made ALL players free agents after each season, and had a random draft order. Yes, it's more work, but what the heck, it would fun as hell. You are playing in 1955, get an awful team, next year get Mays and Mantle, the following year you have to make do with the Danny Murtaughs of the world.
The make all awards winners free agents idea does still have some possibility. Of course people would have to join knowing that they would lose their best player if they had a great season, and so presumably would be okay up front with it. The more serious problem, I think is that it could lead to tanking - you bench Babe Ruth for the last 20 games to prevent his being MVP, that sort of thing. Not sure how to prevent that.
I do think that a strict keeper limit could do wonders, and the number of seasons on the roster limit that DiscoDogs suggests might be the key to real turnover. It does mean some drafting of players with great 5 season records and then discarding, but in some ways that happens in real life as well. It would mean a lot of work for the commissioner to keep track of who drafted whom when and how long they have been on the roster.
What if at the end of each season the two highest valued players (using the following season's salaries) on each team go to the two teams just below them in W-L record (with those of the last two teams going to the worst team and the one with the best W-L record respectively)?
If five years is too many because you can plan too well, what if players are free agents after 2 years on the same team. Yes, you might hit the jackpot and get a player who had two mega-seasons, but only if those two correspond to seasons right after a two-year "contract" ends.
Or a keepers list where you can only keep 5 position players and 3 pitchers each season, the rest are free agents.
In all, while any of these might work, the most fun might just be to let everyone be a free agent after every season, with a random draft order.
When I solitaire play OOTP baseball, I often create leagues, draft a team, then do another one, without playing through the season, as team-construction is almost more fun than watching the thing in motion. Here we could do that and still compete in a league with each other.
Keep me posted and informed please. I currently am not in any leagues, nor running any OL teams, but for something innovative like this I would join up and keep it to this one team eschewing my excesses of the past.