You're the only one here who's mentioned about winning the league though, that's not been the topic of debate. I'm well aware to win the league you'll generally need City's level of finances or a manager like Klopp to be given x amount of years. We're currently light-years away from winning the league.
Though we absolutely don't need £500m to build a good side again. We didn't need it to build Poch's one, we didn't need a comparative amount for Redknapp's one nor for Jol's. A good team can be built by having the right manager and the right signings/ players to fit into his and the club's philosophy. We've wasted money hiring the wrong managers and buying the wrong players whilst seemingly having no philosophy/ identity, hence my original point of spending money isn't the issue for Tottenham nowadays, it's how we've spent it that is.
The obvious point there is that, when Redknapp and especially Jol were in charge, the top four was sewn up based on one part money (Chelsea) and three part red privilege (Man Utd, Arsenal, Liverpool) so it was feasible to break into that based on the stars aligning, as Everton and Leeds managed...once, each, to break the monotony of the same four teams finishing in the top four spots in a slightly different order
By the time Poch arrived the parameters changed, as the top four was a cannibalistic orgy of money (Chelsea, The Sheikh Mansour Team) and red privilege (Man Utd, Liverpool, Arsenal) fighting for four spots which meant there is the possibility of two of those teams cancelling each other out, which is effectively what happened the season Leicester won the league as Man Utd scraped into the Europa League while Chelsea and Liverpool missed European competition altogether to the point neither would have qualified for the ESL if it existed that season
Also, realistically, the issue isn't how we have spent money (Ndombele excepted...) but how we've failed to integrate the money spent into the team. For a few examples
Lo Celso - bounced around a variety of positions he's "good" in, and never given a run in one position he could become "great" in
Sessegnon - played less games at LB than Danny Rose, and Danny Rose didn't play last season
Foyth - played as many league games in one season on loan at Villarreal as he did in three with us
Rodon - starting to swap notes with Paskotsi about how he's an international regular but not getting a sniff at club level
Wimmer - apparently we forgot he was here after his first season
Nkoudou - made Wimmer look ever-present
Llorente - only played when Kane was injured
Vinicius - didn't play even when Kane was injured
Janssen - played when Kane was injured when he wasn't expected to
Gedson - see Nkoudou
We integrated Toby and Wanyama immediately, we took our time integrating Son and Lucas, we eventually integrated Sissoko and Aurier as we needed bodies on the pitch - but that period where Poch was doggedly keeping the faith in the core team even when parts of the team were physically declining in front of our eyes when he could have integrated some players we had, not only did that set us back a year or so in the rebuild but, in some cases, we're still integrating the players now since the ubermensch did such a rotten job
.