Sure, the playoffs started today, but from a Bucks' perspective it's already summertime. Here's a review of key dates and info to prep you for the summer. For a refresher on the luxury tax and the dilemma facing the Bucks, check out this post from February.
April 26: Early entry eligibility deadline. If you're not in by now, you're not getting drafted in 2009.
May 19: NBA Draft Lottery from Secaucus, NJ. The Bucks currently are 10th in the lottery order, giving them 10 chances out of 1000 total lottery combinations. That gives them a 1% chance of winning the lottery, a 3.6% chance of getting into the top 3, an 87% chance of staying at number 10, a 9% chance of dropping to 11th, and almost no chance of dropping to 12th or 13th (h/t SlideRuleJockey@RealGM).
May 27-May 31: Pre-draft combine in Chicago. The all-important measurements will take place in the first three days, so expect those to leak out by the first days of June. Aside from moving the camp to Chicago from Orlando, the five-on-five games have been abolished entirely since virtually no one with a chance of getting drafted was willing to play in them.
June 15: Early entry withdrawal deadline. College players who haven't signed with agents can withdraw by this date and go back to school for one more year. International player can enter the draft up to three times, giving them a bit more flexibility.
June 25: NBA Draft in New York City (6 pm CT/ESPN). Aside from their lottery pick, the Bucks have the 41st pick in the second round.
July 1: Free agency begins, though teams cannot officially sign until the final cap numbers are announced.
Last year the signing moratorium lasted until July 11, though I haven't seen a date yet for 2009. The moratorium runs through July 7, so signings can officially begin on July 8. (thanks again, Dan)
Obviously, teams and players with 09/10 options need to have made decisions by this deadline. The Bucks should be hoping Malik Allen ($1.3 million PO) and Francisco Elson ($1.7 million) opt out, though I'm not sure either will. Elson might test free agency if he thinks he can get more minutes elsewhere, but in this economy I don't see that being a wise move. Allen seems even less likely to opt out, but you never know.
With the Bucks needing all the scratch they can get, replacing both players with minimum contracts would save $1-2 million in cap terms--and since the NBA subsidizes minimum-level contracts over the amount of the two-year veteran minimum, the Bucks wouldn't have to pay more than 825k for a minimum deal. The ideal money-saving scenario would be both Elson and Allen opting out and being replaced by players making the rookie minimum ($457.6k x 2 = $915k total). That would represent a savings of $2.085 million over the status quo.
ESPN Draft Central
'09 NBA Draft on Wikipedia
NBA Master Calendar