Major League Baseball has a lot of complicated rules and procedures regarding player contracts, salaries, free agency, arbitration, and so on. There's certain times players can declare free agency, there's certain times clubs and players can agree to arbitration, there's conditions on how much money a released player gets. You get the idea. I thought I'd try and simplify things by going through the CBA and looking at the MLB Important Dates and 2008 season calendar to try and plot out what will go on when this offseason.

If anything is wrong or I flat out missed anything (and I'm sure there's something on both counts), speak up.

2008-2009 MLB Offseason Dates Worth Knowing

• Starting with the day after the conclusion of the regular season, players can be traded with no waiver rules in effect. It was originally September 29 this year, but with the extra games I suspect they pushed it back to October 1. I don't think it impacted anyone anyway. Trade announcements are probably encouraged to be postponed until after the World Series.
• October 15 was the first date when players with 3+ years of service time who were outrighted to the minors at any point during the season, accepted the assignment, and still haven't returned to a major league roster could declare free agency. Players who were outrighted for at least the second time in their career, accepted the assignment, and weren't placed on a major league roster again could do the same.
• The 1st day after the World Series is the first of a 15-day period during which eligible players (6+ years of service time, no contract for next year) can declare free agency.
• The 16th day after the World Series is the first day Major League free agents can negotiate and sign with a team other than their former team. It's also the first day MLB teams can sign minor league free agents.
• The General Managers meetings are held in Dana Point, California, from November 3-6.
• November 20 is the day teams have to file their reserve lists for all major league and minor league levels. I think that's the day you say who you want to protect in the Rule 5 draft, but I could be wrong.
• December 1 is the last day for teams with Type A or Type B free agents to offer arbitration to them, provided they haven't signed with another team yet. The player would have to accept within a week. If a Type A or B free agent signs with a team other than his former team before December 1, his former team gets draft picks regardless of whether or not they had offered arbitration to the player.
  
• December 4 is the last day to request outright waivers to assign guys prior to the Rule 5 draft and December 8 is the last day to outright players prior to the Rule 5 draft. The Rule 5 draft takes place on December 11.
• Not coincidentally, the Winter Meetings in Las Vegas take place from December 8-11.
• December 12 is the last day to tender contracts for 2009 to guys you want to keep around. There's a maximum salary reduction rule for players under reserve to the club. They must be tendered a contract with a salary that's at least 80% of their salary from the previous year or 70% of their salary from the year before that, whichever is higher. This happened to Rickie Weeks last offseason: the major league contract he signed in 2003 called for a salary of $1.22M in 2006 and $1.32M in 2007. Since 80% of his 2007 salary is $1.056M, and 70% of his 2006 salary is $0.854M, the team had to give him at least $1.056M for 2008. That's what he made last year. Reserved players signed to minor league deals can't have their salaries reduced more than 40% from year to year.
• Between January 2-12, teams must notify players eligible for arbitration that they wish to offer them arbitration. Players can agree to go to arbitration at any time between January 5-15. If a player's salary was increased in excess of 50% through arbitration for the prior season, teams aren't bound by maximum salary reduction rules in their arbitration offers to players. They are still bound by those rules if they make contract offers outside of arbitration. I think it works like this: JJ Hardy's salary jumped from $0.4M in 2007 to $2.65M in 2008 through arbitration. The team could submit a salary arbitration figure slashing his 2008 salary as much as they wanted (though they would obviously not be guaranteed to get it), but if they were just renewing his contract (i.e., neither JJ or the team submitted to arbitration) they'd have to offer at least 80% of his salary from 2008.
  
• By January 18, the team offers and player offers for arbitration are shared between the MLBPA and the MLB Labor Relations Department.
  
• Arbitration hearings are held between February 1-20.
• Injured players, pitchers, and catchers may be invited to spring training no earlier than February 20 14 (45 days before the start of the regular season). All other players may be invited to attend no earlier than February 25 17 (40 days before the start of the regular season). No player is required to report to spring training more than 33 days before the start of the regular season, or February 22 March 4 next year, though inevitable "visa problems" can delay that for some guys. EDIT: Updated because my original dates were incorrect.
  
• If a team and player tendered a contract haven't agreed on a salary for 2009, contracts can be renewed between March 2 and March 11. The maximum salary reduction rules mentioned above still apply. This happened to Prince Fielder last season.
• In order to only owe a player 30 days of termination pay, he must be unconditionally released on or before the 16th day prior to the start of regular season. For next year, that's March 22. Any player released after that date but during spring training gets 45 days termination pay. That happened to Claudio Vargas last season.