While I haven't counted the beans, I suspect from a financial-only perspective it is probably better to win more games and make the playoffs. Keep in mind that losing games affect ticket sales and merchandise during the current and following seasons. Granted, winning games usually means keeping a bigger payroll to keep up the winning, but having played a few seasons here I think I've noticed that I tend to make more money after my better seasons and have a harder balancing my budget after a down season.
Of course, long-term strategies isn't just about making money. There are other trade-offs, such as training (winning often comes at the expense of optimal training), draft pick rank (if you put much into the draft), etc., and depending on where you are in a long-term plan and what your approach to a winning formula is, there are a whole lot of ways to slice this pie. I think most of the best teams in my leagues historically are teams that just burned their way to the top by winning as much as possible (including my own team when I was pretty new here), while teams that toil and rebuild and struggle to make the playoffs (or intentionally avoid them) have a pretty high rate of stagnating or collapsing. But then again, there have been a few teams that have hit my current league in the last few seasons and really did try to win right away and burn their way to the top but then burned their bank accounts into oblivion and ultimately turned bot.
Ah, the fun of this game. So many ways to slice pie. I prefer to just eat it without slicing it, usually starting from the middle and working my way out. And every now and then I have no choice in the matter when some clown hits me with a pie to the face.
Don't ask what sort of Chunks they are, you probably don't want to know. Blowing Chunks since Season 4!