I get the feeling that the reasons for this are two fold: trying to achieve the best value for money and the requirement to still shed dross before spending properly.
In an ideal world, we'd be tying up our key deals as early as possible, but until our long-term situation improves I think he'll only slowly change his methodology.
Brands isn't perfect - nobody is - but on the balance on things I think he's done a fairly decent job and I'm not sure who we could obtain who would do better.
If we're aiming for the long-term, the retention of people like Brands is really important.
I do understand why the deadline day transfers is annoying and frustrating for people, but also understand why it is done.
Football is a game of bluff in transfers. Neither the buyer nor the seller want to be the first to move in the process, and if you are the first mover, you run the risk of the other side really taking liberties. It's really only when there is pressure on, that you see an honesty in the negotiations. I mean take Kabak at Liverpool, Schalke quoted them £30m at the start of the window. In the end they let him go on loan, for 2 million, with up to another £28m in the summer. That deal could probably only have been done right at the back end when Liverpool were presumably saying "take this, or we go to player y".
It is the cauldron that you operate in if you want good deals. Increasingly, the market has gone from massive premiums on deadline day, to really massive savings. Most of Europe want and need to sell to English teams, so panic does begin to set in.
The other point, is that we are not the biggest fish. Players, agents, clubs etc will want to sell to the top pool. In England thats going to likely be Manchester City. After them probably United/Liverpool/Chelsea. Then Arsenal /Spurs. Then we probably come in. A player is likely only going to come here, once he accepts all of the above aren't that interested in him. So we have to wait our turn a bit. Given money will be a lot tighter at Liverpool, Arsenal and Spurs this summer it is a worthwhile ploy.
The one summer we seemed to break this rule, was 2017 under Walsh and Koeman. We got loads in early and it went awfully. So there is a lesson in that- namely it is not always best to do things early.