I am currently at my first year in Panionios, a Greek club with transfer embargo for one year (cannot sign players above 23years old).
I encounter two issues that are really annoying and cant understand the reason of happing, and one detail that you can take in mind for nexr versions. So:
1. Players whose contract left is less than 6 months, cant be approached by my club but other clubs can make them offer. They are under 23 so there shouldnt be any issue, and as you can see below (screenshot 1) other Greek teams were able to make them an offer.
2. After the end of first summer transfer window (somewhere between September - October i am not sure), i agreed to sign two free agents. Of course they couldnt complete the transfer that time as it was outside the transfer period, but they didnt even come to my club at the next transfer window (January) but they will come next Summer! Unfortunatelly i dont remeber the option at "contract start date", just because i know for years now that the default option was "immediate", so whem i made them an offer i kept the default option and didnt even care about it. But now its January and after i saw they hadn't signed yet, i saw that the will sign at 1st July. Even now that i am inside transfer window, i cant make them come now but have to wait till next transfer window (screenshot 2). I know i cant prove it, but i am pretty sure that with a new save with the same club, if you try to sign a player at October - for no real reason - he will not come in January but in July.
3. Less important but same unrealistic as the above issues, when the club has transfer embargo for one year for players above 23years old, you cannot even make offer for player above 23 and make them come after the embargo ends. I could sign now a player 30yo and arrange to come after 1st July that the embargo ends. As i can see, i cant even make an offer at 30 June for a player above 23, just because the embargo ends at 1 July.
My main issue - apart from the frustation - is if issues 1 and 2 will occur only for the first season that the embargo exists, or is a general bug for the club - perhaps due to its embargo - and so their transfers will never be smooth.
Save file is available if needed, but not sure how can it help. It is uploaded via your guidelines and file name is panionios2.fm