I think it's his problem rather than ours. There is a very limited number of clubs who could meet our asking price, and of those one could well miss out on CL football next season. Add in how many of those few actually want/need him, and the choice is more limited still.
The asking price is not something fixed but depends on many factories which cannot be predicted in advance. If the player handed in a transfer request, this would reflect on his price. If he is firm in his desire to leave and is ready to go on strike the price cannot remain the same. Ultimately, the most important thing is not contractual but psychological: how much the player wants out. As regards Berbatov's case, his agent is desperate to find him a CL club and went so far to call Spurs small for his client. As to whether Berbatov himself is desperate to leave, well, time will tell etc.