There's definitely a risk. I don't think anything's a sure thing. The only "comfort" is that all players are created, so hopefully I end up on the good end of things. The odds of finding a young highly rated player with a track record who fits what I want in FA is close to nill, so I'm willing to gamble on the lack of track record. I doubt a Raj or a Sheldon fall to where I pick in the draft, and they're filled out and in theory have less of a OOTP whammy risk.
Vuvuzela and Greenly are both bigger gambles. I think I've spotted something in Vuvuzela similar to when I nabbed Ryan, and Greenly I'm curious to see if I can replicate it considering our team builds. I'm not sure how our parks compare which is a confounding variable. They both fall under Crazy Mach Studies.
I likely don't offer on both without my payroll, but the whole plan would be different. DiMaggio and Ichiro wouldn't be making 20MM each, for one.