In my area most HD is good to 60-80 miles, some to 100 miles. I'm quite surprised that I get WFDD on 88.5 (Winston Salem) in HD, and WNCW (88.7) in HD as well, despite the fact that they're first adjacent, analog reception is sometimes spotty because they're of roughly equal strength in parts of my county, and one is 100 miles, the other 60 miles from me. I think theory dictates that these shouldn't come in where I live. Theory sucks!
There are others I think I SHOULD get in HD, but don't. But I'm not in the target area of these stations. Overall, HD has exceeded my expectations (I live in a DEEP fringe area, and had no external antenna for the first 8 months after I got my radio). I honestly didn't know whether I'd get anything when I bought the radio.
It's all about your individual situation. I would point out that when you don't get a station in HD, it's seldom a signal strength issue, so amps aren't the be-all, and end-all. But a good amp CAN help (bad ones are far worse than none at all). I use a Winegard preamp, mounted to the antenna mast on my roof, and I think it was money well spent. Cheaper Radio Shack amps, and indoor amplified antennas, made things MUCH worse.
Good luck!