[Pelican]

That's an odd experience, for sure. It's possible that the AI may be "saving you from yourself" on those uneven deals. I would not mind a "fail-safe" bar on deals that make no sense, and probably made in error. I will say that others have suggested the AI is not solid on draft pick trading. Probably needs work.

As for trading in general, what are your settings for difficulty and preference? Do you use reputation and "hard trading"? For example, I move the Difficulty slider to make trading harder, and adjust the Preference slider for the AI to favor veterans (so I am more likely to trade vets for prospects). That seems to yield a decent trading process. I use Reputation, but not the Hard Trading (takes too long to work out a deal). And I have the Trade Frequency (AI to AI deals) dialed way down.

Most of my deals originate from me shopping a player. This usually yields a bunch of bad proposals, but maybe one or two that I like. It's a lazy way to figure out a player's worth. And now you can set it to set up multiple-player deals. Or use it as the basis for expanding on the original deal.

The AI is hyper-vigilant about money. You'll find it loves to dump long-term contracts. If you are trading a guy with high salary, you may need to agree to pay part of it, in return for a deal. The AI loves that. My attitude is, it's only money. The owner's money; not mine.

As to timing, I have found that it somewhat mirrors real life. At the end of Spring Training, as teams cut rosters down to size, there can be good deals on guys out of minor league options. Lots of DFA and waiver action. During a season, it slows until nearing the trade deadline. Lots of deals then, and you as GM may get spontaneous offers. As IRL, there are "rentals" of guys with expiring contracts, traded by teams out of contention, usually for prospects. And the AI takes the Winter Meetings very seriously. Lots of deals. Imagine the servers in some resort, running overtime.

Yes, totally possible that the AI would do a deal in July that it refused in Spring Training or over the Winter. That would reflect the changes during the season, particularly a team in or out of contention. Or a rookie taking a vet's place in the lineup. It never hurts to just keep asking.

Another cool tool is the "Make Deal Work" feature. [I don't use Force Trade, which is "cheesing" the game...] Don't take it too seriously. The AI always asks for studs - your best players - when the tool is really supposed to identify a "fill in" that would seal the deal. You invariably get a bunch of quality players, and then a few minor league prospects. As with "Shop Player" patience is a virtue. You may find the needle in the haystack.

I don't disagree that trading can be both "weird" and "inconsistent" at times. But that is intended, I think, to mirror MLB and IRL trades that leave everybody scratching their heads. I don't see it as a flaw.