Not to get in the way of your momemtum, but I'm not so sure Upton's the player you want - especially for the dollars/years it'll cost. He's only got a .316 OBP over the past four years while hitting in a more hitter-friendly one than Safeco. Top of that, he's hit .190 in Safeco with an OPS of .539 in 32 games. Not a big sample, but it would give me pause.
Nick Swisher OTOH, I think is a perfect fit. Can't score runs without guys getting on base and Swisher's very good at it with his .360 OBP. Add in his .287 / .913 OPS at Safeco, and to me he looks much better as an option.
With the current roster, I'd try Jaso in the 1 or 2 hole. He's the only current player who's close to having a .350 OBP. The Pirates did it with Jason Kendall. The 2 spot is tough, but I'd go with Ackley with Swisher 3rd. With Nick hitting behind him, maybe Dustin gets better pitches to see. After that, I maximize my power hitters in the next three slots. The rest of the OF will require somebody to step up - maybe Gutierrez can stay healthy or Saunders can do something. The #9 won't be much more than a NL pitcher as I don't see Ryan becoming any type of hitter. This is what it could look like with simply an investment in Swisher.
Ideal? Definitely not. But it does put your two OBP guys (Jaso & Swisher) in front of your power. Ackley showed me he can hit both in the AFL and his '11 season. Like Lawrie in Toronto, I'm chalking last year up to the sophomore slump.
I don't know if any of this makes sense, but to get two top players on the FA market would be incredibly costly - especially with so many teams with money available to get the price up. And these guys didn't get any cheaper with 37-year old Torii Hunter setting the second-tier bar at $13M per season.
"Chuckie doesn't take on 2-0. Chuckie's hackin'." - Chuck Carr two days prior to being released by the Milwaukee Brewers