Manbearcat
Legend
I hope you’re exclusively talking about a specific party makeup, here. Even then...you’d have to assume a lot of stuff for this to be true. Capers to one side, I’ve been playing in and running successful infiltrations for years in D&D, across 4 editions.
I'm less talking about specific party makeup than you are I believe. What I'm talking about is that D&D features an abundance of focused archetypes with niches and in most of the D&D's history (4e D&D omitted), the lack of functional Conflict Resolution mechanics has served to only heighten the lack of breadth that D&D Heroes are capable of.
This is why in 4e, Fail Forward + Success w/ Complications + Skill Challenge Conflict Resolution + the system maths + easy to obtain rerolls/augments for Skill Powers made 4e Heroes hugely broadly competent. The Fighter PCs in my game were fantastic in climbing walls and absolutely capable of rousing speeches to ensure support from a king and they could sneak as well. This is because of the intersection of all of that stuff above.
But if you remove the stuff that made those things work, then you're left with serious niche protection and heroes lacking broad competence.
How do you get around that?
Build a party to a very specific niche (eg all Stealth archetypes - Rogue, Ranger, Monk, Dex Bard) and deploy that "Score (to use Blades parlance) Strategy" repeatedly. Or you could sub Monk and Dex Bard for Dex Barb and Druid and you can reliably defeat Stealth and Wilderness Exploration and Journeys conflicts.
But overwhelmingly...D&D is going to look like A Team w/ a D&Dified version of plan/approach > conflict with the enemy > complications > shootout/explosions > getaway.
Those are part of the D&D 5e rules, and thus can’t just be glossed over when challenging the notion that D&D can satisfying do heists.
See my post directly above. A game needs much more than just Fail Forward and Success w/ Complications to work (hence why I didn't like 13th Age...which, its Fail Forward approach is very similar to what a 5e game would put forth using the Basic PDF). There are multiple integral parts that turn Fail Forward from dysfunctional (no real mechanical cost for failure, impossible to achieve Loss Con and have story loss imposed) to functional (exciting conflicts with broadly competent heroes who absolutely are risking things and can still lose).
The other part of my post that you're quoting was merely the irony of people HATING Fail Forward and Success W/ Complications when it was in 4e but now suddenly reversing field and espousing its virtues? That is some ironicalizationification if I've ever seen it.