I'm also going to try and hammer this out in one go because otherwise it'll stay a draft forever.
I play almost exclusively with my amazing friends and almost always over Discord using 5e. Even when we're all in the same city we find it too much of a hassle to plan something in person and it always seems like someone has something going on.
Our sessions start in the evening, almost always at the same time, and end 2-3 hours in. In the past I was usually able to get a game in once a week or once every two weeks but my current campaign's pace has been around once a month (mostly because two of my players are also DM's and I play in their games) which is a little disappointing but I'm fine with it being on the backburner for now. Before we actually start there's always 15-30 minutes of unrelated conversation, and when we actually start someone usually comments that "our 15 minutes are up".
I start with a summary of last session and then jump straight into it. For maps I've been using Magma which is basically multiplayer photoshop, this is something new I'm trying out (so far its been going well). Before I used no map and just described things in combat, but that got hard to track and I always needed to remind people of where everything was. I don't use any other bots or websites and I've been thinking about trying music but haven't looked into it yet. On my side I use only two websites: google docs (for all my notes), and fantasy-calendar.com (self explanatory). All my notes are spread out among many different documents but I usually have a doc for my notes/current events in the world, one with some random tables (but it's mostly just lists of ideas, not stuff I would really just roll on), one with all of my monsters in it, and one for whatever dungeon/quest they are on. A few days (or a week if I'm not feeling that enthusiastic) after the session I write down what happened in Discord as another way to remind people of what happened.
Between sessions my planning is quite sporadic and is motivated mostly by random inspiration and running out of things for my players to do. Usually I try to have the next 2-3 sessions planned in some form but this varies. I don't really plan things out beyond 5 sessions (too chaotic and too far away to really feel excited about it). I make almost everything myself, I find pre made adventures (especially anything WOTC makes) clash with how I want to run things, and even though I read a lot of blogs I find that I rarely take anything wholesale from them. I have an incessant need to tinker which usually means I'm adding and changing things up until it hits the table.
My campaigns tend to be long, usually a few years and over 50 sessions but I have considered doing shorter, more focused campaigns recently. When it comes to choosing a new campaign I list out around 4 ideas, explain them a little bit and have my players vote on which one they want to do. Since my campaigns are so long I've only done 3 of them (counting the one I am currently running) so I don't have any standard procedure for how I set up the campaign other than not prepping enough and prepping in the wrong areas but that should get better with time.
My games lie between the more player/story focused style of 5e but also incorporates a lot of OSR ideas into it. In practice this looks mostly like 5e but with a bit more problem solving and less straightforward stories. Or maybe its OSR with a lot more drama? Its a bit of a mess but my friends like it and that's the important part. Characters have pretty big backstories and I use them to help shape the world (in my current campaign everyone's character is death themed which was not planned but ended up shifting the campaign in an interesting direction). There is usually no goal for the whole party to go after, instead everyone has there own goals which sometimes conflict with each other. We also use a lot of homebrew, most of it coming from one of my DM friends.
If you're reading this you should also post about how you run your game. I'd love to read about it!
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