People keep saying #1, even though no one has ever said otherwise. But a team doesn't have to be one player away in a rebuild to pursue the best available talent.
You may be right about #2, but is any free agent a year from now worth a bigger investment by the Red Sox? I'd argue a few middle infielders may be more worthy, but they don't fill a major need by Boston... unless it's a splash -- someone who can make an impact on and off the field, change the clubhouse culture, and put actual fans in the seats.
When the Rangers signed ARod they were a losing team in fourth place. He was great, but his chemistry didn't enhance the team enough.
The 2002 Marlins also finished with a losing record in 4th place, and the following January signed future Hall of Famer Ivan Rodriquez. That signing seemed odd, since IRod replaced Charles Johnson, also a Gold Glove All-Star catcher. Then the Fish won the World Series.
When Dombrowski signed IRod for fourth-place loser Detroit in '04 it seemed even stranger... but two years later he was in another World Series.