Ultimately, where we are is a product of 3 things.
1) Taking to long to start the rebuild/ poor pre-rebuild decisions.
I was ok with us trying to keep the streak going, but once it became clear the cupboard was bare because so many of the late streak picks didn't pan out, we needed our 're-tooling' to also have an eye on the future. By the time we starting accept where we were, we had very few really salable assets and not much in the pipeline. Obviously Larkin pick was great, and Mantha, Bert, Nyquist, Tatar and AA all were good trade chips, but our D-core was moribund and with nothing on the way.
2) Lottery luck - not just talking continually moving down, because in a couple of those years we still made great picks, but also being at our worst when overall the drafts weren't great. Sure we whiffed on a couple of high picks, but they were also weaker draft years, so less top players to hit on. A little earlier we could have been on the McDavid etc drafts, a little later the Bedard etc, but we were worst and had negative lotterly luck in weaker draft years.
3) Flaming on FAs - partly poor choices, partly limited pool due to a) Weak team b) higher tax c) reluctance to hand out 6/7/8 year deals. Yzerman chose to avoid some better players in the aim of not being handcuffed by bad contracts when our top propsects come of age. Short term pain for long term gain in theory. Much will depend on how we do with FAs once the likes of Danielsson, ASP, Cossa are on the team and we look like a team with a short-medium term future.
Last year getting into the playoffs would have been nice, but wouldn't really have made a serious difference going forward. Ultimately, this rebuild rests on the guys who have already been drafted but haven't yet cemented themselves as NHL-ers