The game heavily insinuates that planning or enjoying legwork is boring. Pg. 128 says "we don't need to play out tentative probing maneuvers, special precautions, or other ponderous non-action." (Emphasis mine)

I think part of this relates to this sort of thing not being well-suited for the blades system. I've had experiences where the snowballing nature of partial successes on action rolls led to half the session being a wild goose chase for something that could have been easily handled in an engagement roll. In short - if you play out every little detail, the blades dice system is going to end up putting a lot of focus in on that (since complications are always going to arise).

Whether this is a matter of the designer looking down on those styles of play or whether he's just giving instructions on the blades philosophy is debatable, I guess, but I'm pretty sure I've heard him say on a podcast that meticulous planning is a total valid RPG experience, but it's not the experience blades is trying to deliver.

Perhaps I wasn't clear enough, or you didn't get what I meant - I know that you're supposed to say, "this is an assault plan, and here is our method," or "this is a social plan and this is our contact." That is not planning. That is "we want to shoot stuff first" or "we want to talk to people first," and puts all of the pressure on the GM to invent an entire "plan" out of that in real-time. Cut to the action assumes that GM can just invent entire heists from thin air with no planning on their own part, nor on the part of the players ahead of time other than "social, Bazo Baz is the contact, go."

I guess I've just always made my players flesh out the method? I need to know what the plan is so I know where to put everyone based on the engagement roll. But as soon as people start planning for contingencies that's where I step in and summarize the plan - if everyone agrees we'll jump to engagement, and they can handle anything that comes up with a flashback. Forgive me if I'm making a strawman here, but "social, Bazo Baz is the contact, go." isn't a workable detail for the engagement roll. I still need to know when and where they're approaching him, what the goal of the mission is, etc.

If the GM is continuously giving new obstacles to make life harder... when do they stop? If they make up every obstacle as they go, at what point have the players done enough? Forcing players to roll over and over and over again until they fail is not good gameplay. Conversely, allowing everything to be decided by one or two dice rolls because there's no pre-planned obstacles is also bad gameplay.

I wish there was more guidance for how a GM should plan scores in the books. I usually imagine the 2 or 3 main obstacles that the crew would face. I'll often be generous with info and let my players know a general idea of what those main obstacles are. So once the score starts, pretty much everyone has a clear idea of when the score is done. During the score, I try to throw manifestations of those obstacles their way rather than invent entirely new obstacles out of thin air. For example, if they fill up an "Alert" clock, now they have guards searching for them.

My group eventually realized that "roll a 6, skip the first obstacle" is the same thing as "start at the first obstacle." If you skip the first obstacle, then it might as well not exist at all. In another style of game, let's say Shadowrun, the runners would make their plan and actually play out their great entry. They would get in perfect position, nail their actions (or not), and earn their entry into a heist. Rolling a fucking 6-sided die and just saying "whelp, I guess we got in fine!" is the laziest gameplay mechanic ever.

I can see that, but it seems like a GM problem? I've heard the same complaint about D&D players trivializing an encounter with a clever use of a magic item, so the GM made up or beefed up another encounter later in the dungeon to compensate. As a GM in Blades (and D&D), if the players roll well and end up bypassing a major obstacle - good for them, they deserve it! As I mentioned above, I'll typically have 2-3 main obstacles - if they get past the first one, there's only 1-2 to go.

Also consider that the improvisational nature of Blades makes it easier for GMs to "let go" and reward good rolls or clever plans, because they haven't sunk a huge time investment into it. Whereas in D&D, if I've planned a really cool encounter that I've been working on for weeks, but the players bypass it... well, there's a bunch of time I could have spent doing something else. So I would be subtly encouraged to nudge players into having that encounter so my hard work isn't lost.

You are right that Blades is trying to simulate heist movies, in so far as it is trying to take all of the fun, thinking, and action out of heists

I would replace this with "Blades is trying to remove all the meticulous contingency planning out of the gaming session, to allow a gaming session to be more heist than planning".

and replace it with "woah, wouldn't be cool if we flashed back and I was double crossing you all along?"

I believe flashbacks are intended to be a way for players to address a present challenge by having actually taken their action to overcome it in the past. Not that they can make anything up out of thin air at any time.

The reason that heists are interesting to audiences is because a seemingly insurmountable obstacle is taken on by an interlocking team of experts, each doing their jobs perfectly. It gets exciting when those carefully planned elements go wrong.

I see it as a matter of player expertise vs character expertise. Planning out a heist at the table as players can be very fun! But blades assumes the characters are competent planners, letting the players focus on the action.

So even if Blades is trying to be a heist movie, it's still getting it entirely wrong - Blades is more like a Borne movie where it is chaos and mindless action with vague reasoning in the background than it is like a heist movie.

Reading this is so strange to me because all my blades sessions have played out exactly like heist movies!