One of these years we should throw in the wrinkle that the commish picks like 10 numbers out of a hat (1 through 312) and those 10 players have a season ending injury.
This would reward teams for having depth at each position and would mimic real life even more!
I really like this idea. I'd broadcast the drawing over skype.
Just for fun I generated 10 numbers from random.org and got the following players out for the season:
Dwight Howard
Monta Ellis
Caron Butler
Taj Gibson
Ed Davis
Ersan Ilyasova
Travis Outlaw
Antonio McDyess
2 players not yet taken.
To change things up, I first sorted by first name, then assigned a number 1-312 and ran it again:
Stephen Jackson
Shawn Marion
Marshon Brooks
Marcus Camby
Kris Humphries
Jrue Holiday
Deron Williams
DeMarcus Cousins
Chuck Hayes
Amare Stoudemire
I'm not a fan of the season ending injury idea.
1. Not all players are equally likely to be injured, thus an even drawing won't be all that realistic.
2. GMs already consider injury history when they vote, no need to further simulate things
3. It would make the game a whole lot less fun for potentially 10 out of 24 GMs. I mean if Kobe, Pau Gasol, Wade, and LeBron were all to blow out their ACLs via this lottery that'd be terrible wouldn't it. 
4. Seriously any first our second round pick knocked out would just eliminate a win now team from contention. That'd suck and be unfun. GMs wouldn't be rewarded as much for depth, but instead they'd be punished by randomness.
The reason I think it's a good idea is that it makes the Celticsblog draft that much more realistic.
Folks may factor in injury
history they don't factor injury
possibility, and therefore routinely & grossly underestimate the importance of team depth.
(BTW I think Ainge has been guilty of this over the past few years too.)
You're right that all players aren't as likely to get injured -- there are some that are injury prone and some not -- but guys get freak injuries all the time. Heck just look at the Celtics recent past:
- KG's knee injury that kept us from our 18th banner was a freak thing. NO ONE was factoring in that he could get hurt that summer during CBLog draft.
- Perkins' knee injury in Game 6 of the 2010 Finals likely keeps us from winning Banner 18.
- Rondo's injury this year drastically affected the MIA/BOS series.
And yes an injury to a 1st or 2nd round pick would hurt a "win-now" team but so would said injury to a real NBA team -- see again KG's 2008-09 injury or Chris Paul's knee injury (or even Udonis Haslem's injury for the Heat this year). Each of those 3 injury's were "freak" in that none of KG, CP3 or Haslem has had a significant "injury history" that other GMs would factor in during voting.
I also think while it might bite for a team with a high pick, the important flipside is that it levels things for teams with late picks and gives more folks a legit shot at winning/playoffs. (as someone who's had 1st picks in the 20s the last 2 years it makes it much much harder and feels sort of like whoever gets the top 3-8 picks are the only ones with a shot...)