When is the best time contract-wise to sell a player?

I play a low rep club and naturally every good player I sign inevitably wants to leave after a while or demands too much money. I usually sell them when their last year of employment starts, but I was wondering if I'm doing it right? Is the time left on contract influencing their price?

Or maybe I can sell them just 9-10 months before the contract expires (when the season is underway) and set the transfer date to "end of season", so I'll have them for the full duration of the contract and still get the transfer fee? Won't the AI teams decide to hold out a couple of months and sign them on free transfer?

I've never really paid attention to how long a player has left on their contract. I always try and tie players down to long term deals if I feel they can be key for a few seasons. Even, if after a season they are no longer a key player, I could still look to sell them if they have done well. As a lower league club you should always be braced for a high turnover of players. The fact of the matter is players at that level or some, will get too big for their boots. I will always find a player better than what I have. So if a club does come in with a reasonable offer, I will sell. Even if they are a key player. With contracts though, I would always sell with a year left. Especially if you don't have any chance or only a slim chance of keeping the player. The money is much better. I don't think you are doing anything wrong though and every player or potential contractual problem should be dealt with differently .

While playing FM06 as Thurrock, when I'd recieved a bid for my player on summer window I just changed it to be done at the end of the season They always agreed on that. Even if the player was on his last year of contract and they could make a deal in January and get him for free That gave me: happy player + the key player for another year + time to find a good replecament. Don't know whether it works on FM11 though.

I think if im right that a players value decreases heading into the last 12 months of his contract. So if selling is what you want to do then maybe the last 18 months or 2 years of his contract would be best to do so.