A shopping trip can kill half a session if it’s been a while.

Do you really have fun running a session like that? Me and my players would die of boredom.

The biggest challenge during Tier 4 is still resource attrition. Let them use their big spells, but don't let them rest. The best challenge you can give them at this point is to make a multi-session-spanning dungeon-like structure.

An example from my previous campaign: heroes needed to get to the lowest level of Hell, but they needed to transit through every one of them in process. Enemies were everywhere, and places for rest were virtually nonexisting. I think they had like 1 long rest in four months of play during T4, and it actually was hard for them.

When I did play 5e IRL, I used Ard sheets, tweaking them in Photoshop or Illustrator whenever needed.

The worst thing is Bob doesn't know he wants to play something other than D&D.

Where is this jail cell? What’s the city name, vibe, etc?

That's a bad question, because it draws blanks, not leaves them. Better questions would be:

• «Fighter, how big is the city? Is it more like a village, or something closer to a big, prosperous metropolis?»
• «Rogue, which known criminal is doing his time in some other part of this jail?»
• «Barbarian, you've been there quite a lot for your drunken fights, did you? Name one guard who's here now, you know each other a little too well!»
• «Wizard, for what breakthrough the local magical academy is known?»
• «Cleric, which religion do they preach here?», and, optionally, «Which part of it you would never agree with?»

Don't just ask «what's the city vibe», get them something to build from!

Still, memes likes this one actually breed such GMs, because somehow they think it's funny.

Odyssey is pretty lackluster after a certain point (authors really overdid selling their names on the cover, while the actual adventure is... well, a little better than WotC ones). But at least it has a brilliant active community around it on Discord, so should you run it, you'll have tons of support from fellow DMs.

Most people just want to do cool shit.

There are THOUSANDS of other games, and most of them let you do cool shit instead of tracking resources. Just, you know, stop playing D&D.

As a DM, I cringed at this. Alright, you broke the game, overshadowed your martials and blew past the encounter your DM spent so much time carefully crafting. And your game session ended two hours earlier. Thanks everyone, see you next week I guess.

Shame about removed monsters. I personally used all these Arch-Devils, and Boreas basically became a father figure to a lot of PCs at my table.

Wicked Ones

Describe the place they are leaving. Ask them how do they feel about that. Then do a montage of their journeys (just a couple scenes) and ask someone to pitch in, like «Ranger, what's totally unexpected grows here?», or «You see a small pillar of smoke, seems like there is a small village off the beaten path; Cleric, who do they praise here?». And after that you can tell them «...so, you're here».