HERE'S THE TRICK
I use Spurs too. (currently 3rd season)
sold Palacios, Jenas, Naughton, Dos Santos & Keane on the first season,
sold Woodgate, Cudicini, Hutton & Gallas on the second season
sold King, Bentley & Pav on the thrid season
...not much of a Spurs team now obviously
but the core thing is to place as much player on sale as possible in one go and place them as Not Needed by Clubs on the Transfer Status. Set them as Transfer Listed with unspecified sum and Loan status as Unavailable. Yes at most times they will offer fee slightly lower than the market value but hey if you are down the same route like me, with the money you got from the players sold plus the given transfer money from board, you just get yourself enough dough to add 2 to 3 quality players in your team in exchange.
And of course, that does not resolve your offer just like I did with Keane in my first season, I just offered to clubs with a lower fee with "Not Needed by Club" status, that status should be enough to attract one or two clubs given that he is good enough for a lot of teams.
Players like Keane might as for a weekly fee as a compensation till the end of his contract as they move to a lower-rep club, but they usually cost just as much as a rotation or backup player. Get the transfer dough and buy someone better!