I always go for the rebuild in all my sports games. I'll make a few trades and free agent acquisitions to start, then sim the first season (sometimes two) so I can get right to the next offseason(s) of extensive roster turnover. Then I start playing in year two or three.
I can't believe I haven't been whisked into an actual front office position after having brought numerous Stanley Cups to teams like the Oilers, Panthers, and Jets. Not to mention all the Super Bowl rebuilds in Madden.