And again they are starting with 5e, ffs.

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.

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.

Girl by Moonlight's space mecha setting isn't much about mecha fighting, it's more about politics in an enclosed space (I was a playtester and have run a pretty number of games between all the playsets there was).

Beam Saber is more about mecha fighting, and it uses the same engine

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.

Seems like you're confused, because we're in the blades in the dark sub.

I would go the Scum and Villainy way. If you play a 'monster' race, replace your starting ability with a 'Xeno' one. Player and GM should work on it together. Quote from the rules:

If you want to play a xeno with unique abilities, replace your starting ability with the following: “Xeno: You may spend stress (0-2) to perform an inhuman feat only members of your species can do.”

Wicked Ones