I actually think it is this thought process where we need to be braver in the future.
I would ask fans to really ask themselves what we really got from Toby and Eriksen after these key moments where we were scared to sell them. The answer is not much. The reality is that Toby was pretty average towards the end of his Spurs career. Eriksen played for that last 18 months with such a can't be arsed attitude and frustrated all of us. They weren't worth more on the pitch than in our transfer kitty at all.
There is also an element of failure from our recruitment teams that scares us in these situations as well. It basically took 5 years to replace Walker with Porro. Trips didn't step up from his backup, and Aurier was a mess. Emerson failed whilst perhaps KWP and Foyth weren't given ample opportunities to win the shirt. After the RB debacle, I can see why we were scared to sell. No different from my old man telling me how he watched our double 61 side get replaced one by one with lesser players.
However, that is still not a good reason to shift players when they refuse to sign new deals and start running down the clock. We need the money in our transfer kitty, not players that aren't all in. .