Hey yankeesfan1024! I was just working on a new post to submit and then I saw yours, so I hope you don't mind another newbie hopping aboard your train...
If any Veteran level OOTP player is reading this, I'm sure your eyes will be rolling as if your head were a slot machine in Vegas. I'm aware that you've all been through this and
maybe even worse if previous versions of OOTP were even
less trade-friendly than OOTP 20/21. I'm frustrated as I'm sure other n00bs are too. I totally understand why the AI will ask for a lot in return in some cases where I have approached them.
Some. What I'm hoping for is maybe a tip or two on how to lessen the blows newbs, like myself or yankeefan1024, feel from the AI. There have been two times where I almost resorted to Seppuku for being unable to secure a player I promised my home market fan base.
I've been playing OOTP for less than 2 months and that's probably why I still feel frustrated with the AI GM's. One reason why I say frustrated is that I've read many posts where people say things like, "just don't take advantage of AI teams in trades". Well, that certainly won't be a problem on my end. LOL I also want to make clear that I play with just about every OOTP option set to default. One or two settings may have been adjusted, like roster size for my Short-A and Rookie teams, but I do not weaken the AI's play anywhere. Totally pinkie swear.
Some observations I've made... When an AI team offers me a trade they will offer a player of varying degree, but what they want in return is usually preposterous. If they're offering me a 3-Star player they'll want a 3-Star player in return along with a 2.5-Star player or maybe two 2-Star players. If I propose a trade, asking for one of their 3-Star players the only way they'll accept is if I give them a 3.5-Star or 4-Star player in return.
I understand that any team, IRL or AI has the upper hand if I propose a trade for one of their quality players. But when
they approach
me asking for a 3.5-Star to 4-Star player, you would think I would now have the upper hand. So far, 90%+ of suggested trades by the AI have wanted the world for almost nothing in return to my team.
Finally, I've noticed that the vast majority of players the AI offers me are playing in the last season of a contract. So, I might be looking for a pretty good RF and I'm willing to give up more than I should - A
little bit more, you know... The player offered in return might actually be surprisingly not-terrible

but he'll be in his last year of a 3-year contract making $450,000 (1981 signing) and due to his not-terrible performance I know he's going to want an 8-Year deal worth $900,000/year minimum. I have been such a terrible money manager in my first few seasons as a GM, but some contract requests are going to be impossible to meet unless I don't mind not being able to hire a new batboy let alone a single free agent for 2-3 years.

Now, that's 100% my fault, but I think I'm learning...slowly...