IMO, you're going to have to replace the two oldest pitchers next season. If you had 20m in training, maybe you could squeeze another season from them. So, IMO, you need a plan for next season to replace them. If you get a decent pitcher via draft/IFA this season, he'll be ready to replace the 36 y/o in a couple of seasons. If you sign a 31 y/o FA this season, you'll be 20m before his decline starts. And he'll hold his value for the full 5 seasons. But, yeah, replacing 1-2 guys at a time instead of 5-6 is so much easier. I generally plan my teams 3 seasons at a time. If I'm in S31, I want to know what I'll need after S33. That way I have S31-S33 to figure it out.