The question of choosing a good bar is not which is more upmarket, but what kind of tension you need for the night.
A great night and a comfortable night are not the same thing
Hotel bars have good lighting, service, views, and a sense of stability. Neighborhood bars offer a comfortable distance and the fun of becoming a regular. One is not superior over the other, but their purposes are different.
new perspective
Bar selection is more about emotion than the rating of the place. For tense anniversaries, a hotel bar is the way to go, and if you want to slowly build up your taste alone, a neighborhood bar will last longer.
Practical method
For a first date or anniversary, a reservationable hotel bar or lounge is recommended, and for a light second date, a highball bar or local cocktail bar is recommended. If you drink alone, choose a place with a counter where you can comfortably distance yourself from the bartender.
Things to watch out for
The prices and service charges at hotel bars can be burdensome, and the atmosphere at neighborhood bars varies widely. If you're going to a place for the first time, it's a good idea to check the menu prices and operating hours first.
A good bar is not an absolute ranking, but is best when it suits the purpose of the day and my condition.