first question: was 2010 the first year for the six speed?
opinionated question; what's the best year (engine) for the money? looking to buy used in the mid to upper $20k range, 4x4 screw 6.5 bed, tow package, wiling to sacrafice some miles to get a decent package. any thoughts are appreciated, thanks.

 

2009 was the first year for the 6-speed in the F150. Engines were the 4.6 or 5.4.
2010 brought the new brakes and electric fans, which were a substantial improvement.
2011 brought the engine changes: 3.7, 3.5EB, 5.0, 6.2.

There's nothing wrong with the tried and true 4.6/5.4 platform. I would get a 2010 at a minimum for the brake improvements.