I accidentally visited the Richmond Hill a few weeks ago. I shan't get into too much detail, but I work for a certain cruiseline and ended up hanging out at the pool bar. As expected, there was a wedding in progress, but it wasn't annoying, ie; drunken fools running amok, etc.
I've been reading the prior reviews of this place, and I suspect they've been written exclusively by low-budget American tourists who haven't been outside the confines of the Lower 48 before..
The Inn is LOVELY, and the aforementioned 'weird' owner is quite gracious and charming. If you check their website, (just Google it for God's sake -- I'm not posting a hyperlink) a double room is $90 (US) off-season and $115 during the winter. From what I experienced there, I'd be glad to pay it. Even in the middle of the day it's idyllic up on the hill -- the breeze, the pool, the RED STRIPES, etc.. Yes, it's slightly funky, but so is the rest of the island. If you're gonna go to Jamaica, don't expect to be pampered -- just be cool and everything'll be fine (hopefully)..
Montego Bay is an absolutely gorgeous place, but it's corrupt beyond belief. It doesn't have one of those "hide the women and children" vibes, but it's pretty intense. Yes.., everybody's hustling, but on the other hand everybody's pretty much starving. Extreme poverty is always around the next corner..
Regardless of whether or not you stay within the loosely defined tourist areas, you WILL be panhandled, offered every drug imaginable, and given grief for "not supporting the locals" if you don't care to purchase overpriced trinkets. However, I have never felt threatened in Montego Bay and I wouldn't consider this a problem -- just a fact of life.
If you stay at the Inn (which I intend to do SOON), hook up with a licensed Juta Tours cab driver. Don't mess around with the shady cats in the white Toyotas, as you'll end up negotiating (read: paying whatever they ask so you can exit the vehicle with all limbs intact).
Be smart and enjoy.., Mo Bay rules!
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.