I've just been using chain salons for over half my life, so I'm used to strolling in and getting a quick, cheap cut and being done with it.
Lately I've had an urge to get a better quality haircut, but I just can't bring myself to walk into a barber shop, for some reason. No idea what to ask for, or even if I need to call ahead.
I get anxiety over the weirdest shit
There's no wrong way to drink a drink you bought, people have seen worse than whatever you're doing. I couldn't name more than a few whiskeys myself, so yeah "bottom shelf/whatever is cheaper" is a super appropriate answer. If your friends make fun of you ask them to pay for the top shelf ones.
The rest... yeah whatever you like. It's your money, it's your drink, do what you want. But bartenders should know what tastes good what doesn't. And being more of a regular is going to help you avoid being upsold or anything like that. You might even score free drinks now and then.