I've been playing a LOT of nerd games this past few months. I haven't been running a lot, but I've been playing a lot. I've come to the conclusion that much like anything in life you need to understand what your expectations are going into something. Sometimes that requires a few tries at it to make the decision. I've also come to the conclusion that its not always the system that changes how much fun I have or my expectations, it's the company.
Whilst that was mildly vague I will attempt to explain.
I've been running 5e with some friends at work and been having a grand time. I am using the basic rules, and running it very much like an old school DM. Theatre of the mind, way less "checks" for everything under the sun, hand waving things like travel, combat is quick, etc. We have been having a LOT of fun. We haven't been using any grid, or roll20 just talking it out over google meet.
I've also been playing on and off with the Google Grognard chat (yeah that's what I'm calling it). More often than not we are playing Old School Essentials, with rotating DMs and it is always fun. The guys are fully aware that I'm the guy who always pulls the lever, the guy that always starts shit, regardless of the character class that I am playing.
Last night I played in my second game of "out of the abyss" on roll20 with some acquaintances. it was infinitely boring. First off I've played this adventure before, the first part sucks donkey wang, trying to get out of the prison. The last time I played I committed suicide by jumping off a platform because I was too frustrated with the railroad. All of the guys I'm playing with know the rules inside and out, and know how to power game everything, including extra attacks when beside other players, etc. It's a board game. With moments of roleplaying.
Know what is my expectation here? I like all these guys, there fun. We do get right down to gaming however. What I want to do is have fun and get the other players having fun. that's not too much to ask right? Right.
They had fun. My cleric was knocked unconscious in the first battle, and I spent 1.5 hours listening to the rest of them play.
Was it my fault I did something rash? Probably. Did I make it fun for other people? Not entirely. Did I have fun? nope. Am I playing again? I'm going to say nope, but I'm an "obliger". Which means I'll probably say yes.
If I was playing a different class would I have fun? Possibly. Although I decided the party needed a heal bot, so that's what I went with.