Was the Ottavino trade worth it considering how close it got the Sox to the cap? If we stay under, the money part is not a big deal, unless it kept us from getting someone better. (We would likely have not traded promising prospects, anyway, so I'm not sure the money was the main reason we did little at the deadline.)
What the Richards deal a good deal? It sucked, but so did Kluber, who was the guy many felt we should have gotten, instead.
Has Perez been worth his contract? Easily, yes. His first 11 starts were priceless, and got us to the playoff slot we currently hold. He didn't need to be started so many times, recently. That's on Cora/Bloom.
Was the plan the FO had for the OF a good one? Better than "good." It was excellent and still is, IMO.
Are you ok with them not getting a veteran backup in the offseason? Yup, considering the budget and counting on Houck & Seabold as depth.
Several people questioned the SP additions (as always), the RP additions, the lack of a 3rd OFer, the lack of a reliable 1B.
I did, too, but with a limited budget, Bloom had to roll the dice at the positions he thought could get by in-house. Not all did.
1B: Dalbec, Marwin> Failed
OF: 3rd OF'er was Cordero> Failed/ 4th was Kike (Arroyo at 2B)> Worked
SP: Worked for 2.5 months, then failed, and now is showing some renewed hope.
RP: Far exceeded expectations, until just recently.