Good points. I like having some high-floor guys signed, and that's exactly what they've done with Ashby, Pratt, and Lara. It provides roster and payroll certianty, and of course, buys out FA years. But like we've seen with the Dodgers and all of their guaranteed contracts, or a team like the Phillies, who were begging teams to take Nick Castallanos off their hands; having guys locked into roster spots also takes away flexibility.
My point isn't that they should/shouldn't try to extend Made, but rather that there are reasons you don't want a bunch of guys getting paid a big league salary while they are on the IL, or spend time in AAA.
The risk-factor with extending Made for $150M, compared to extending Lara for $30M is pronounced, and yet currently, their floors are about the same. That is expected to change pretty quickly, of course, otherwise this wouldn't be a topic.
I guess what I'm saying is that signing Ashby, Pratt and Lara to their extensions is risky because you need to roster them, but signing Chourio and/or Made means not only rostering them, but starting them every day. I don't think Made is there, yet, for the World Series Champions.