Lots of stuff in there, and in most of your posts .. honestly mate, if I read you correctly, you have lost your faith (and all the conversations in the world may not change that, and be careful personally with that)
Let me try to add a little more detail
When I talk about trophies (or lack of) in regards to our history and/or other teams, it is to ground us on the fact that "it isn't we are doing something wrong and as soon as we correct that (or buy x player) we will suddenly revert to some winning Spurs team that bags trophies", we need to break new ground, to become a big/elite club (not just one with elite potential). Money may not score goals, but better players do, and better players cost money (bit of irony that Ajax best CL run in years ended against a similar level team with a slightly more expensive squad)
To the point of the past 5 years, could/should we have converted one of the SF/Final/PL runs into a trophy? in isolation, yes, no question. What does that come down to? manager/player inexperience, failure to invest at right moments, opposition simply better, luck, brick refs? To me .. life just is never as simple as one thing, its some combination or all of the above.
To your broader question of the future, i.e. when do we win, when do we peep out. Spur's fans need to understand a very uncomfortable fact, in my opinion (solely mine) Daniel Levy realized a long time ago that in the short term, Spurs simply cannot compete (a fact that West Ham, Saudi Sportswashing Machine, Southampton, Everton are still failing to grasp) for top honors. What does this mean?
- It means it was not the time to risk/spend when the gap was not close enough
- It means settling for "good enough" results as long as it kept the club progressing to the long term
- It may mean giving up short term opportunities at glory for the future of the club and the opportunity to be that elite club.
Tottenham has a plan, and the plan is most likely on track (and this is the big difference when people try to compare us to the Scum "settling for 4th", the Scum were regressing from contenders to desperation to keep a revenue stream)
- The 4 years before Levy Spurs finished between 14th - 10th
- Within 5 years, we were "best of the rest" and competing for European competition for the first time in decades
- Another 5 years had us in CL first time
- Today we are CL regulars (4 in a row) with a CL final run
- In that same time, the facilities (training & stadium), the squad, the fanbase (over 200 official global supporters clubs now), the profile and revenue of the club has increased remarkably (statistically I think only United have improved their financials at same or better rate)
- Clearly a plan with NFL, naming rights, Rugby and other non-football related events to drive even more revenue.
Will Daniel Levy spend a 100M+ and back Poch this summer to push on? I really don't know, he may still feel we have a revenue gap to continue to close.
Is Poch the man if he was to do so (guess what this thread is about)? I don't see the risk/reward payoff in changing him right now
Will Spurs be a bigger club with likely the results that come with that in 5 - 10 years? = absolutely, we are better placed than any other club in the world to improve our position.
So my suggestion to you is, understand the game is rigged (the rich stay rich, the poor get poorer) but we are very well managed and doing our best to become something more (no longer speculation, the stadium, revenue, results show that Levy got it right). Does that mean we may be frustrated a few more times, a few more years where we are almost there? where we get annoyed about the squad depth, that one more player that could have made the difference? Maybe, maybe the successful Spurs will not be the one of Kane, Eriksen, Dele but another one (just as the CL regulars wasn't Berbs, Keane, Modric, Bale)