If I'm going to ask the player to do something multi stage I will usually flag it so they know that there's a few places where things might go wrong. "OK well sneaking up to it is going to be the first hurdle; after that you're going to need to figure out how to get the giant lizard to cooperate as you smuggle it out the back".
That lets the party start thinking ahead a bit, so maybe the illusionist says "how about I conjure the smell of something delicious wafting in from out a back window – that way when the rogue manages to sneak up and untie it it'll hopefully pop right out the window by itself".
Whereas if after the stealth check succeeds you give a bunch of subsequent unexpected checks the player might feel a bit aggrieved that you hadn't signalled how much work it'd be (especially if it uses skills they aren't good at and would have avoided relying on).
I basically agree I think, or at least agree to within normal-group-variance. Which is to say, at least with my friends, is someone said “I want to roll stealth to steal the lizard,” the DM would probably say something along the lines of “it’ll be more complicated than a single roll, you’ll have to get in there, get the thing free, there might be unforeseen problems (it is a barely tamed lizard monster after all).” I think we would probably not need to be warned in the first place and would go right into planning the heist anyway, because who doesn’t love a heist?
I think the specific thing I didn’t like in this example was the presentation of a specific path to the player. Although taking a second look, it seems the autoDM just presented it as a potential path, so maybe it isn’t so bad.
That lets the party start thinking ahead a bit, so maybe the illusionist says "how about I conjure the smell of something delicious wafting in from out a back window – that way when the rogue manages to sneak up and untie it it'll hopefully pop right out the window by itself".
Whereas if after the stealth check succeeds you give a bunch of subsequent unexpected checks the player might feel a bit aggrieved that you hadn't signalled how much work it'd be (especially if it uses skills they aren't good at and would have avoided relying on).