Agree with your overall assessment but its harsh to say they choked in 2016. I would argue they were never really in the title race at all.
That team was still very early in their development and kinda just fell into 2nd place when all the rest failed. They were always a good number of points behind Leicester, I'd say they did pretty well that season they just fell off as they just were not ready. If anything, it was Arsenal who threw a golden chance of a title challenge away (they were the only ones with a stable team).
Spurs downfall is traced back to 2018 - they had fallen slightly from their 2017 points total and that was the time to invest - they didn't and the rest is history.
We always have to be mindful of this and invest when it is possible to do so. Of course we have a much stronger squad and coaching set up so we are in a far better position.
whether it’s harsh or not - the whole point is - they
should have been in the title race that season - Leicester won it for goodness sake
That’s the point, it was the prefect storm.
As for early development, not sure I agree with that, plus - you can counter that with the ‘but Leicester won it for goodness sake’ argument, what sort of development where they in, with a coach who’d been there less time than Pochettino had at Spurs. Spurs had the likes of Lloris, Eriksen, Walker, Rose, Alderweireld, Vertonghen, Dembele, most of them had been at Spurs for at least a couple years, most of them experienced players in their prime. As well as Kane, Alli, Son, Dier of course. They had a really good settled squad with a settled manager / coach
It was a massive missed opportunity.