As to your second paragraph, the Brewers can afford a lot of undervalue contracts, but they can only afford a few market value contracts. They need to get undervalued players wherever and whenever they can. If you lock up players at market rate (which will occur if you wait until year 2 or 3 of arby to sign the extension), then you end up in a situation like we just got out of, with most of our money going to a few aging guys and no money left over to fill in the holes. Then you become completely reliant on your farm pumping our starting quality MLB players every year or you end up playing guys like Yuni B and Overbay (the second time around). Signing a player at that stage is effectively the same as signing a free agent, and smaller-market teams can't build a roster that is too reliant on free agency. But if you don't lock up good young talent, you better have the best farm system in MLB for many years running. Because you would need to rely almost 100% on the system producing 2-4 MLB ready players every year. And even at that, it would be very difficult, at best, to be a winning team consistently with a roster filled 100% with players that have 5 or less years of MLB experience. It's a little different that just signing FA off the street because those players are going to be a little older. If you like the projection of guys like Villar, Broxton, Arcia, etc. I think signing them to 5/6 year contract after 2-3 years of service time isn't a bad way to go. You'll never get it right 100% of the time, but a team like the Brewers need to roll the dice a little on a few manageable contracts. I'm not even saying the guys I mentioned necessarily, they're just examples. But what if a Hader, Ortiz, Woodruff etc. looks really good after 2-3 years? Top end starters cost a fortune, so to me it's worth signing them to an extension if you can. Devil is in the details, of course, in terms of dollars involved.