Hard to complain much about adding an 8M pitcher as competent as Hill who really pushes guys like Wilson and Thompson away from the rotation (and Thompson still has 3 options left, so he'll definitely be ticketed as starter depth in AAA if that matters). I do have some scattered thoughts that are probably something like nitpicks:
1) Hill has never been the most durable pitcher, and innings stability is the biggest thing the rotation definitely needs IMO. If he can give you 160 (or the rough equivalent pace, assuming he's ticketed to be traded), that's perfectly workable, but there is a little bit of risk that he could be out of commission for a month or so early in the year.
2) Again with the one year deals, though obviously Hill is probably not getting 2-year deals anywhere. This is a bit of a separate issue, but I almost wonder if Reynolds' trade request threw a slight wrench into the plans. It's well within the realm of possibility that BC never intended to sign a multi-year guy, but the way things are shaping up right now has this season looking like a "let's improve while also having some veterans to trade off, our best player to sort out, and a lot of money coming off the books next winter".
3) I'm resigned to it, but a little bit worried/frustrated at how the rotation depth seems lined up to push Ortiz to AAA until Super Two clears for him. I'm sure there's an argument that with his lack of experience in the upper minors, the polish will be good for him, but based on stuff, he's a better option than Oviedo and certainly Velasquez, who it sounds like has a handshake deal to start here.
We'll see - I'm not too worried about depth questions because they have a way of working themselves out with pitchers. I do have to wonder if it wouldn't have been better to just take some combination of these moves and invest the money into a mid-rotation workhorse type guy over 4 years. The payroll space should be there, or we're just joking around.
I'm open to the argument about flexibility and at the end of the day I guess there's no getting around the reality that we're a back-to-back 100 loss team who is chasing 75 wins as a start. There's only so much excitement that is possible in an offseason... finding some way to get back to the table with Reynolds, or full and completely pivoting to get Cruz signed long-term are about the only things that can do it. Otherwise, I am looking forward to a team that will be more watchable on paper, knowing that it will be frustrating if guys like Endy and Ortiz are held down in AAA. Flexibility should also give you the option of rewarding prospects with MLB playing time, and I don't think there's a better use of a "meh 75 win" season than starting to get some experience for guys who have to be big contributors ASAP.
Final thing is that I am pretty curious if we'll make one more somewhat notable position player signing. The OF is crowded, but Cutch still seems easily doable on a 1-2 year deal. Maybe a guy like Pollock has some upside left and will be looking at one year offers.