[Charlie Hough]

Welcome to the community! It's always good to see new players getting into the game.

Winning is definitely more fun, and I'm highly competitive, even with a baseball sim, so here's how I play:

I use higher trade difficulty, and I use AI talent evaluation settings that put a heavy emphasis on ratings over stats. This creates more of a challenge, and it allows the AI to make much smarter transaction and lineup decisions. Since the ratings drive the sim results, within the overall league totals and probability environment, it makes more sense to emphasize ratings. Otherwise, it's too easy to make good trades with the AI, and it will make a lot of bad decisions with player personnel. But other OOTP users do things differently.

I don't play in challenge mode, though, since I want to use commissioner mode, in case I need to use the editor or settings to fix a problem in the game. But I've rarely had to do that. Usually it's to fix a problem with an AI team.

I typically play career historical games, although I've done a few career fictionals. But I also manage all of my teams' games in one-pitch mode (one payoff pitch per at bat), so it can get really frustrating if you're managing a losing team. Over the past couple of versions of OOTP, I've preferred to find historical teams that were around .500 in the standings, and I try to see if I can win the division, win a pennant, or even get to the World Series with them. I've had my best OOTP experiences by doing this, especially with historical minors enabled, as some of these teams had some good AAA players that could help the cause. I've won some World Series, pennants and divisions with a number of these teams, and it's a great way to create a challenge while still giving yourself a good chance to win.

If I'm going to manage a losing team that will take years to improve, then I might manage some of the team's games but simulate certain weeks or even months, if the team is doing poorly and I'm not having fun through all the losing. But you can still focus on making trades, drafting rookies, watching the daily waiver wire, managing your rosters and minors, and doing all the things to help build up your organization. Then, when the team is really ready to compete, you can take over more of the individual game management and play out entire seasons, if you prefer to play that way.