It's never too early to discuss (even when you're in the middle of a playoff run). If I'm Walt, here is what I do and the order in which I do it. All four are mutually exclusive options, meaning if 1 then no 2 or 3 or 4. If 2 then no 3 or 4, etc.
1. Address the Ryan Ludwick situation.
Try to exercise his $5MM option. If he wants more money or a multiyear deal, the most I'd offer is a 2-year deal in the $8-10MM range. If he wants more than that, I let him walk. He is already in his mid-30s and the Reds should have a LF ready by 2015, whether that's Lutz, Rodriguez, or maybe even Winker (not to mention Frazier). If Ludwick signs, great- there is not much that would change on the roster as Frazier would become the everyday 3B. If he doesn't, go to #2...
2. Try to trade for Justin Upton
The Diamondbacks will look to trade for a SS this offseason, and they'll probably have to overpay. They've already indicated they will explore trading Upton this offseason. He is owed $38MM over the next three years, something the Reds could conceivably afford- particularly if they let Stubbs and/or Bailey walk. I'd offer Cozart, Stubbs, and their choice of any prospect in the system outside of Hamilton and Stephenson (including Corcino or Cingrani). D'backs get their SS for the next five years, their CF for the next two, and a top-flight prospect. Reds get their LF and cleanup or #2 hitter for the next three years. Win-win for both sides. If it works, Frazier still plays 3B.
3. Sign Kevin Youkilis to a 2 year $10MM deal.
The erstwhile Red Sox hero gets to return home to finish his career in front of his parents as he has said he prefers. He bats cleanup and plays 3B for 100-120 games to keep his legs and back fresh. He plays against all LHP. Henry Rodriguez spells him against tough righties for 40-60 games a year. Youk also plays 1B when Votto needs the occasional day off. H-Rod plays 2B when Phillips needs the occasional day off. Todd Frazier becomes the everyday LF.
4. Trade Drew Stubbs, Homer Bailey and their choice of prospect other than the big four (Hamilton, Stephenson, Corcino and Cingrani) for Matt Garza and David DeJesus.
Provided Garza proves healthy in the offseason. The Cubs get salary relief in a year they are not going to compete (2013) by dumping two free agents-to-be. In exchange they get two slightly inferior but cheaper players who are signed beyond 2013, when they are expected to compete. In addition they can pick whatever prospect they like in the Reds system outside of the big four. They were dangling these two in a package to the Reds for Stubbs and Hamilton at the deadline. Now with a shorter window until FA, they settle for Stubbs, Bailey, and a good prospect. The Reds improve CF and their rotation, while gaining another LH hitter. Reds can make a qualifying offer to Garza after the season to get a high draft pick and let both players walk in free agency to be replaced by Billy Hamilton and either Corcino or Cingrani in 2014. Reds add payroll for 2013 only but shed it in time for Votto and BP to get expensive and Latos and Leake to get their big arb raises.
LF Heisey (maybe see if one of the youngsters like LaMarre or Lutz can make the jump)