Spurs under Levy are always going to struggle to compete with clubs with Middle East money, or oligarch owners, or established commercial operations like United. He is playing a longer game of financial sustainability based on his income from the stadium. Spurs's big spending splurge was based on the money they made selling Bale, which was a record at the time, and it took them a while to see the benefit of that - the consensus was that they brought in too many players all at once. They then reverted to type and spent at a much lower level until 17/18 when they did well to get £47m for Walker. 19/20 has been their biggest net spend for a long while, most of that going on Ndombélé, who's now being thrown under the Mourinho bus.
Their ownership and spending model look more like Newcastle under Ashley, but with Levy being more actively involved and relatively successful in the transfer market - in that respect, he's a better businessman and owner (whatever the view of the players now, Alli and Dier were bargains and have been good value). They would do better if they developed their academy players better instead of just cashing in on players, given that they don't have the resources to compete with the top EPL clubs, and in that respect Pochettino was such a good fit for them.
Pochettino probably squeezed as much as he could out of his squad given his spending constraints. I was surprised that they went backwards to the extent they did in late 2019, and they clearly need an overhaul that probably needs more money than Levy is prepared to spend in the short term. He's gambled very heavily on building revenue from the stadium with an underperforming team.
Levy's blind spot is his managerial appointments - Jol, Ramos, Villas-Boas, Sherwood, etc. I think he's got it badly wrong with Mourinho, who is surely going to throw his toys out of the pram before long when he doesn't get the huge sums he will want. I can't think of a more unnatural mismatch than Levy and Jose.