I've never understood why the Burnett signing sticks in your craw so much. He wasn't really retired, though he considered it. The Pirates hadn't made him a QO . And he wasn't signed to a multi-year deal, it was a one-year deal with a one-year mutal option (which was not exercised). It also wasn't really that expensive, $7.5 million with incentives that reached $12.75 million, which he reached because he pitched more than 200 innings (which he did while pitching through a hernia instead of missing two months, a decision that didn't do much for his performance or for the Phillies). Plus the team had already budgeted to pay Halladay $20 million in 2014 (though I think it was clear he wouldn't trigger that option by the end of 2012).
Not a great signing, but more because the Phillies should have already been rebuilding by then, but Middleton and Monty and Amaro weren't ready. He was also a panic acquisition (because of Hamels being banged up in ST on top of Halladay's retirement and Lee's issues).
I think AF is overly worried about this sort of thing but the 2013-2014 team is exactly what his biggest fear is, so much dead money and high service time vets that you can't really add good talent and wind up settling for the likes of Revere, Byrd, Burnett (of course they also chose to spend all their cash on a closer and stick with Utley, Rollins and Chooch around then).
I agree there is no downside to giving a 26 year-old $100 million. It's an acceptable risk and if he fails the $ is still not going to prevent the Phillies from spending in 2021 and 2022, unless there is a huge failure of the homegrown talent, in which case they have bigger problems.