SI, please improve/clarify player happiness for future games.

Here's my problem:

My goalie, Stefan Frei, has been wanting to move to a bigger club. This all started about two years ago when he came to me with his concerns about wanting to move to a bigger club. I told him to wait and see how we progressed. A year later and we were roughly in the same spot (reputation-wise) and he asked to be transfer-listed. Reluctantly, I agreed...even though the club was in the semi-final of the CONCACAF Champions League. Fast forward a few months and, after rejecting three offers of mutual termination (silly player, I sure as heck aren't going to pay you to leave the club!) we overcame the odds to hang on for an aggregate victory on away goals in the final. Lo and behold, Frei no longer wants to leave the club. Great!

Six months or so go by, and once again Frei is asking for a transfer. I agree to list him (at his market value, no less) and my team wins MLS, then finishes third in the Club World Cup. Things are looking up and, despite being ranked 27th in North America (and still improving) Real Madrid knock on our door and offer Kaka. We jump at the chance and, after doing everything we can to find the necessary funds, sign him to the club (this is 2014.) It's now approaching the end of February, and here's Frei's information:

General Happiness: Doesn't want to leave club.

Unhappiness Reasons: (Concerned) Wants to move to a bigger club.

Short Term Plans: Considering his options.

Head Coach Promises: Feels time is running out for his head coach to sell him.

Good Relationships: Is pleased that Kaka has joined the club.

So...does he want to stay, or does he want to leave??? I transfer list him by request and yet he doesn't want to leave?

Fairly understandable.

On one hand he is ambitious and wants to move to a bigger club but on the other he is also loyal and settled at his current club.

This is very similar to how a lot of people feel when they get offered a new job IRL.

Personally first time I would do what you did but second time I would have let him go. At this point I would have set his asking price much higher than his value and then offered him out to encourage the transfer. As it stands you are going to fail your promise and this will lead to more unhappiness.

This bug has been around for a couple of FMs now and I'm surprised that SI hasn't sorted it out yet.

Fairly understandable.

On one hand he is ambitious and wants to move to a bigger club but on the other he is also loyal and settled at his current club.

This is very similar to how a lot of people feel when they get offered a new job IRL.

Personally first time I would do what you did but second time I would have let him go. At this point I would have set his asking price much higher than his value and then offered him out to encourage the transfer. As it stands you are going to fail your promise and this will lead to more unhappiness.

Well, Basel stepped in and offered $500,000. We settled on $600,000. Sigh...now I'm stuck with him on my roster until the transfer goes through on June 10. Guess I'll toss him into the reserve side and let my youngsters fend for themselves in net.

Update:

Great...just received a message from my assman reminding me that I promised to get rid of Frei in this transfer window, and that he might get upset if he doesn't leave. Umm, he does realize that the transfer has been agreed upon, right?