A good night out is about the company you're with not where you are (to a certain extent).
Yes I find bottom of town shite, in fact I find most of Old Town pretty spectacularly bad. I've been to plenty of places in other cities and towns where the location was hyped up/played down and have had mixed nights out in either such location. The best nights are when you're with a decent bunch of people and you're all having a laugh and not worrying how crap/good the next place is supposed to be.
The thing that really gets on my tits are the people who moan there isn't much to do in Swindon compared to other close-by Cities and Towns. There are plenty of varied things to do, just not in as much quantity as surrounding places. Anyway it's easy enough to get to other places if needs be.
This post would be a hell of a lot better if it was a drunken rant, but sadly I am not drunk. Probably because the bottom of town is so shit

Good post Simon, and sums up my feelings. People moaning about nothing to do need to get a life. There's a great saying, "If you don't like something, do something about it". If town pisses you off, go and live somewhere else and then moan about that within 6 months.
FFS, you go anywhere for any amount of time and it becomes crap, my mate moved to Marbella and came home after a few years because "it was shit and there's nothing to do".
As you state, it's not where you go, it's who you're with. I have had great nights in some fucking shit holes, i've had shit nights in some swanky establishments. When i think back to the best nights i have had, there's no real common theme that can be attributable to all of them apart from the company i keep.