To railroad or not to railroad?

I was particularly impressed with the way Yesterday's Tomorrow handles setting up a oneshot mission. They players choose their playbook and then the players say why their the mission needed a character that fits who they are. This way you don't end up with missions that don't cater to the players, or a player being left out.
Each player adds an obstacle that they are uniquely suited to overcome (the reason they were hired on in the first place) and defines --roughly-- how much of a challenge it is (and therefor how much of a reward they hope to get).
If we have a driver-type character, their player says why a driver was specifically needed.
I have tried to adopt this mechanism into all my games. "Why do they need a necromancer?" "Really? Why did they hire on a sewage process worker for this job?"

Nice -- I've been meaning to pick up Yesterday's Tomorrow. Gregor Hutton, is that right? Sounds a lot like the setup in The Sprawl when I played that, thought maybe a little more direct about the roles that characters are to play in the adventure.

And thanks, @adam for shedding some light on the 5e side of things. And yeah, my "what now?" question about battle maps was more for live play than PbP, now that I think about it. And I know there are loads of sources for maps as well, so grabbing something appropriate probably isn't that hard when you have a little time.

The few times I've gotten into that sort of situation, I'll either run it as theater of the mind (I can usually see important battles coming and have a plan for them) or I bring out my foldable dry erase. While I prep combat, I hand a marker to whoever is nearby and say "Draw a map of how the scene looks in your head" and use a circle with a letter for each character.

It ain't much, but it's honest work ;)

My formerly-IRL group is like this. They prefer to be taken for a ride. Our games really bog down when whoever's turn it is to GM just leaves things wide open and lets them do anything they want. Granted, this happened very rarely. But now I'm GMing the group, and on PbP, no less, and the times I've tossed them in the sandbox for even a limited time I could almost picture this deer in the headlights look on their faces.

As you like to say (and I definitely agree), many ways to play! As long as the group's having fun, right?

Not that one. I refer instead to the one by Stras Acimovic of Scum and Villainy/Band of Blades fame. https://offguardgames.com/more-games/
The Sprawl requires the GM to make the mission make sense around the player characters. I have seen this fail when the player had a different idea of what they character meant/did but did not speak up.
Yesterday's Tomorrow assumes oneshots, or single/few missions with a character. The character advancement rules are optional. This transience is rather common in Cyberpunk, YT puts is front and center.
It does work with longer games, but needs a bit of effort. That is part and parcel for all World of Dungeons games: they are meant to be quick.

Sandboxes are 'boxes', they have clear boundaries. Set the boundaries for the players so they know where they stand. It is less scary that way. Give them something to shoot for... if they want to.

Yeah I tried that, too. I've seen it work with some groups but not this particular group. I've played with these guys for 34 years and I think they've gotten to a point in their lives where, at the end of the day, after slogging through work and finally getting time away from the kids, they really just want to throw math rocks and wreck stuff, you know?

Many ways to play.

Ah yes -- I was thinking of Remember Tomorrow, and forgot that I not only had Yesterday's Tomorrow, but had intentions to run it! Love virtually every WoDu hack I've run across. My favorite kind of PbtA. Will re-read...

Yup -- I've seen plenty of examples of these types of players. Keeps the GM on their toes if they have a mix of them and much more proactive types who want to drive the story and even the setting. Managing that can be an interesting challenge, not unlike having a mix of player types at a live table -- those who want to immerse and only speak in character, those who never do that, and everything in-between.

Even a normally proactive group can sometimes feel like being spoonfed for a session. It can be tricky when they don't let the GM know beforehand (maybe they all arrived and discovered they felt that way?) and a pantser suddenly needs to plot, live, with everyone watching them.
It can be useful to have a few model railroads in one's back pocket for such occasions. Maybe integrate a one-shot adventure into a regular group.

The players in my party have very rarely ever gone off the always-present rails (not that I force them there, but I have places I'd like the story to go and they follow along). They generally just like to experience a story, kill some monsters, and get loot.

I think that's how most people want to play it. I think what gets most DMs in trouble isn't players staying on a story, but when they solve a puzzle in a way you never would've expected, or befriend the lieutenant of your Big Bad, or blow up the whole city or some nonsense. Then you have to figure out where to go from there.

And honestly, I get the feeling that's part of the fun of being a DM. It's a lot less stressful with PbP, though.

Big agree -- and I think 'playsets' can really help as well. Barebones but evocative settings that come with named NPCs, a few locations, factions and how they feel about one another, current events, etc. Present a number of different angles to the players -- even before the start of the session or game -- then let them pick from the limited menu, and even create all-new dishes.