The whole selling process will be being handled by a big agency, sure DL will do the deal but he won't be the one holding pitch meetings with the marketing teas at X,Y,Z .... loads of companies have done 'research' on the value of naming rights Duff and Phelps came up with this: Man United are top of the list with £26.75m, followed by Man City at £21.9m, Spurs, then Liverpool on £16.9m, Chelsea on £16.75m, and Woolwich on £16.65m.
The best time to sell anything with a marketing angle is just before a major event ... my guess is that just prior to the first NFL game is favourite ... but that's a pure guess.
We are not the first to sell naming rights and we will have learned from others mistakes ... don't take the first offer and don't tie up the deal to tightly. Woolwich's first Emirates deal in 2004 (100m for shirt and stadium sponsorship over 10 years) looked good at the time, but just a couple of years later it looked terrible and by 2014 it looked like the worst deal ever made .... hindsight is a wonderful thing
So rushing into a deal just when the club is gaining momentum isn't necessary ... wait, negotiate, build in all sorts of increases and get the best deal possible ... if that takes two years plus then fine, far better that than rushing into a deal that ultimately costs you 10's of millions in lost revenue down the line ....