Boston is an interesting example. As is Pheonix, just for the FA factor. Boston has lost several. Pheonix added several (plus some trades).
I brought it up once and I'll mention it again -- selection committee. A committee of knowledgable hockey people (it is open to debate who this would be) could sit down and discuss this. i.e., it is reasonable to think Boston will not do as well given the losses to their roster, and reasonable to think Pheonix will improve. it is reasonable to think Tampa (since people are sick of Detroit as an example) will be better than Washington, etc...
You discuss it. You sit down and rank the teams based on factors such as recent history and how they seem to be trending from last year to this year, as well as over the last several years.
Everybody on the committee cranks out their own list. You average out the places for everyone (could even toss out the highest and lowest ranks for each team to get a more acurate figure).
Finally, you do a weighted lottery based on that list of 30.
You can't account for the "what if player X got injured" scenario. You just can't do it without playing games. The fact is player X didn't play and didn't get injured. Using that as an excuse to give all the teams an even shot is absurd. Giving an even shot to everyone ridiculously overcompensates for almost any "what if" scenario. You can't account for these factors without playing games. Period. That isn't a good reason for the even shot for everyone.
Remember, this isn't just about Crosby and the number one. They'll have 30 spots to fill. Not just one.
Try not to imagine your team getting the number one. Think about your team getting number 30. Then think about how fair that is (depending on your team).
Finally, as to the whole post-CBA, team X is going to have to cut half its roster scenario and then team X will suck - well, we'll cross that bridge when we come to it. We all know that the CBA will come before the draft. Once the CBA arrives, we can look at how it will immediately effect teams. Until then, we have no clue.
We can debate the draft order because we have a feel for how that works. We can't really debate the immediate roster effects of the CBA because it relies on a lot of details we won't know until a CBA is signed.