I agree 100%... no make that 120%. You'll find lots of people who disagree with that standpoint and I've personally been in VERY heated discussions (not as much on these forums, but for other similar sports sim games) where my "adversaries" INSIST that it's just not possible to make challenging AI for a game like this.
My "regular job" work involves creating a sort of "AI" to control real-world processes, so I know that premise is completely false. In my AI systems, the computers are as or more efficient & effective than human operators at doing WHAT WE ASK THEM TO DO. Just don't ASK them to do something they are not GOOD at doing.
Yes, it can be difficult to program solid AI... but it is far from impossible. Really the secret is to start with "less is more" attitude with respect to AI. I.e., restrict what you allow the AI to do to eliminate any "stupid" things it does. Then slowly add more and more AI functionality, ensuring each step of the way that any new algorthms don't cause old ones to "break". If done carefully, and to a master plan, eventually all the "little bits" of AI add up to one great big bit of very good, rock solid AI.
It's like's Ohms' sig, which I like a lot. If you code the computer PRECISELY with the right "rules" to follow... you'll end up with solid algorithms in the end.
That what shouldn't you ASK the AI to do? Don't try to code complex human-rationalization type "rules" because by definition, they ARE NOT going to be precise enough and you'll find unexpected negative results arising from all sorts of unanticipated scenarios. That's what we HUMANs excel at, not computers.
Instead, base AI decisions on the data available... let the computer number crunch and gain its competitiveness from "knowing" the exact "values" of it's own team worth... talent of players in the league... et cetera. Protect the computer from making stupid mistakes.
The one example I've given on these forums numerous times is when the computer trades away a front-line starter and has no suitable backup available in-house and also has no Free-agent alternatives. Let's face it... even if the "value" recevied in terms of prospects exceeds the value of that one player... this is NOT a good move for computer AI to undertake. Yes, you can argue that maybe the team is "rebuilding" and reducing team payroll and nebulous concepts like that.... but that's the problem... don't ask it to mimic a human GM. It in fact isn't going to have enough "awareness" to plan out and execute a strategy like that.
Those are HUMAN reasonings and THAT sort of AI programming is going to be difficult if not impossible to implement correctly.
So the simple restrictions of (1) don't trade away starters if it leaves a gap in the starting lineup and (2) don't acquire talent if there isn't already a gap in the starting lineup (your original post example), takes away a lot of the scenarios where the current AI makes "stupid" decisions.
Yes, I've gone on a rant... but this is my own personal saop-box favorite and it bears repeating this message once again. The road to better AI is really to allow it to do less and when it evaluates player "value" (which in a vacuum it seems to do pretty well). So no matter HOW good a particular player is based on his talent alone... the computer AI needs to recognize that that value diminishes to the computer's team even to the point of ZERO if that good player would be the 2nd, 3rd, 4th best player at that position within the teams organization.
OK, I feel better now.

But in summary... yes I agree with you entirely. I play these games to be challenged and want to feel a sense of accomplishment when I'm actually able to beat the computer. I am not a historical simmer and I get no pleasure from playing "god mode" and just setting up things and watching them run whilst intervening to make up for any AI shortcomings.
Edit: I think to some extent Clay is progressing towards a philosophy similar to what I've described... simply because I SUSPECT the addition of depth charts might be to eventually help the AI figure out exactly what assets it really has and therefore whether any particular addition to the club really adds value or not... but that is just a theory. I have no insider knowledge whether that's the case or not.