Funny how we all think differently. I've never had anyone ask me to cut into my steak at a restaurant, and never thought about it. But, I'm with Margi on blue steaks (the first time I heard that description for very rare I cracked up)(It was a French waiter in Hawaii, if I asked for my steak blue around here they'd ... well, they already think I'm a little crazy, this would erase all doubt). I want it seared on the outside, warm through, and that's it. Anyway, I'd prefer the waiter ask than to have to return the steak. You can put an undercooked steak back on the grill, but you cannot uncook a too-well-done steak. SO I never bother to return a steak that for me is over-done. By the time I get my meal, the rest of the table is done. If it is a place I plan on returning, then I make my displeasure known to owner, manager, or maitre d' (I've finally lived somewhere long enough that I can actually wait and do this at a different time so I don't cast a pall on our dinner party). If I'm just passing through, I don't bother. A waiter asking me to cut into it might actually give the restaurant time to grill me another steak (or put someone whose might be under-done back on) before the entire table is finishing their meal.
I rarely do a good steak at home simply because the quality of the steaks is better at restaurants, and since I don't do them often at home, I'm worse at judging the steak's done-ness than any restaurant!
I can't see finding a waiter's "Is everything OK?" as an insult. It sure as heck beats having a person at the table wanting another drink and having to crane your neck to find your waiter. If I didn't want the attention of a waiter, I'd eat at home. I like eating out, and want that attention.
Now, this is with the understanding that I'm not talking $100+/plate restaurants where you have a waiter dedicated to your table or maybe one other, with no turnover, and all the chefs are that, high end. There's no place like that in the entire tri-state area (and, yes, I've been to them).
And, Margi, I LOVE steak tartare and carpacio.