Before Levy you have to go back to the mid sixties to find when it was better. However, Levy has set the bar so high he is a victim of his own ambition. With little patience a lack of progress is not an option. If he can't stick he has to twist.
His decisions from a football point of view are questionable because they are intrinsically linked to finances, i.e. spend the Bale money all at once because if other teams know we have spare cash they will attempt to over-charge us in the transfer market. Noble but floating somewhere between realistic and paranoid. Most clubs are going to try to over-charge Spurs anyway. The outcome of the spend, spend, spend under AVB was a team that doesn't know each other and are struggling to gel. Just like Bruce, Paulo DC and quite a few others before, it is not going to happen immediately. 12 to 18 months will be necessary for the necessary understanding between new team-mates to develop.
To compound the issue he chose a manager who tried to make the players fit a system rather than design the system to suit the available players. Much of Redknapps success came from letting the players do what they knew how to do rather than impose a system. Redknapp was a strange choice, he was probably the only manager that Levy chose himself because he was forced into a corner. The football was threatening the financial stability under Ramos and Redknapp had a track record of rescuing those in trouble. The downside for Levy was that Redknapp refused to work with a DoF, which took Levy out of his comfort zone. Levy likes to use a DoF to advise him on footballing matters, probably to avoid letting the football cloud his financial judgement.
Great signings are not like London busses, nothing for ages and then all coming along together. They are few and far between and need to be picked up when they become available or at an opportunistic time. Levy missed a trick with Real Madrid, if they had been so hell bent on signing Bale , then he should have shoe-horned a decent player or two out of them rather than taken the money and run. He screwed them into the ground so far they had to part with one of their better players to our North London Rivals to balance the books. A pyric victory at best.
Levy strikes me as the kind of guy who will have a price in his mind when he goes in to buy or sell a player and then sticks to it. A great technique in a horse auction but footballers aren't horses, a player is worth how much you need him and how much to selling club need your money. Daniel Levy is now going to have to be very careful with transfer dealings and in choosing his next manager, Uncle Joe is either very patient or silly and I doubt if it's the latter. He is however probably guided by the bottom line, which could easily disintegrate with the wrong choices.