Was just offered Reyes and B.J. Upton for Jimenez, Santos, and Ichiro.
If I go through with the trade it will basically end my chances this year likely...my pitching staff would hurt badly, but I truthfully don't need Santos and Ichiro is getting old as it is. On my projected keeper list would be Santana, Hosmer, Cano, Longoria, Phillips, Reyes, Desmond Jennings, and Hamels.
Would my pitching staff suffer too much next year? Should I worry that much about Reyes injury history? Thoughts?
First, you need to make a decision. Is Reyes (and Upton I guess) worth giving up the season for? He's had two hamstring issues in close succession. If he can't run, he can't steal. He's a great player, of course, but you would take on some real risk.
Ubaldo is a great arm but he has proven not entirely reliable after a good year. Reyes, despite his injury issues, is a better keeper than Ubaldo. Therefore, on paper, Reyes is the real win here. As you've already mentioned, your pitching will be horrid next year.
But see, I think Upton is a pretty decent enough guy to keep. You also have two solid second baseman, while others are likely begging for at least one. This means you have some chips to use for a pitcher.
I think that Santana, Hosmer, Cano/Phillips, Longoria, Reyes, Jennings, Hamels, and some pitcher (gotten through Upton or 2B trade) looks quite good. I would make the trade and worry about the pitcher later, but first I would decide on whether this year is an option.