I've mentioned this in some game threads, but I'll consolidate some here.
1) DOB jinxes the living shit out of everything. No-hitters, shutouts, good road trips, you name it. Am I stupid enough to believe it matters? No, I'm not. But it's annoying. When an announcer plays it close to the vest, it's like "we're all in this together...no one say anything!"...it's part of the fun, part of feeling like you're part of the broadcast, in on the joke. DOB destroys that in a way I don't remember ever hearing from any other announcer (and I'm old).
2) DOB often uses awkward phrasing (e.g.; "Off the Green", "Bases filled Up", "pop" instead of "fly" and vice-versa) and mixes up known tropes like he's playing a game of Mad Libs (e.g.; "lasers a shot" or "hammers a drive"). I am especially attuned to shit like this, and it infuriates me (I recognize this doesn't necessarily reflect well on me, but fuck it).
3) "Swifty." Fucking die (figuratively)
4) DOB often uses statements without meaning: "The key to Buchholz' recent success is that he's been hard to hit"
5) DOB (or his producer?) is in love with streaks and statistical oddities like 20/20 seasons. He seems to have an agenda for each series and pounds the living shit out of it.
6) DOB cannot shut up about player struggles (or good streaks)...he seems very recency-bias driven, and it gets annoying.
I like DOB as a person from what I know of him, and have a shitload of respect for him as a father and human being, but I simply do not enjoy his work. At all. And I certainly don't think he compares favorably to Orsillo as a broadcast talent.
In closing, I would point out that when people say stuff like "well everyone bitched about Orsillo, too", they neglect that the giggle-fests were usually in games where we were getting pummeled (and people will bitch about anything in those circumstances).