I agree with your basic premise, OP, that the team would be much better served by missing the playoffs and getting the 10th or so pick vs making the playoffs, getting our aces handed to us in 4 more ultimately meaningless games and getting the 15th or 16th pick for our troubles.
It's a cute story that the little team that could actually made a playoff push and likely made it, but it's an obviously pyhrric victory all day long. It's like offering a little kid a quarter today vs offering him a dollar tomorrow. One is obviously the smarter move, but the kid just doesn't care. He wants what he wants and he wants it now.
The thing is, I think Danny was completely on board with tanking this year, and something changed to make him make the IT trade. I think the Rondo and Green moves were clearly with an eye toward the future that Danny expected to result in more losses.
This is pure speculation, but I think the thing that changed was Stevens, and whether he was willing to go along for another tanking year. All the trades pre-trade deadline this year were with an eye toward accepting a lottery year this year. None of them had to do with improving *this* year. The IT trade was about improving this year and beyond, and it was a gamble. I doubt Danny thought that the IT trade would result in as dramatic an improvement as it has. I think he thought IT would be a good piece (consistent with a constantly upgrading your assets philosophy), but that he would not be good enough to actually get us out of the lottery this year. He reckoned wrong.
But I'm with you about knowing that a better pick would have put us closer to our next championship more than four more meaningless games. That's just plain obvious. That's the quarter to the dollar analogy. Short term, ultimately meaningless gratification vs having a better asset going forward.
As to Philly, there's no way to judge the success of their strategy right now. One thing I do respect is that they had/have a strategy, and they went all in on it and didn't half ace it. Whether their strategy is successful or not remains to be seen, but you need stars to be a real championship contender in this league, and the draft is one way to get them. There are no guarantees with any given strategy.