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I found the recently released Cost of Annoyance, or the Hidden Cost of Changing a Game to be a fascinating watch. Yes, it is talking about updating video games rather than tabletop RPGs, but everything discussed here felt so pertinent to the changes happening with the remaster.
It discusses the 'but I don't want to change' feeling that many customers go through, but also why change is often necessary. It discusses how to make a change that become more welcome to your player base, or how to highlight the benefits of a given change.
As an aside, one section discussed the problems that happen when designers must make a change not to benefit the player base but to please corporate overseers, which made me think of the WOTC OGL debacle, and then of PF2's need to excise exclusive OGL content from its newer products in response.
Please feel free to view and discuss.

Mathmuse |
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I like Extra Credits videos, though I like their spinoff Extra History more.
I will start off by being an old fogey.
Regarding the QWERTY keyboard, the typewriter in my childhood home was an old Underwood typewriter that my grandmother had picked up secondhand, so it was primitive. I had to press each key 2 centimeters downward to hit the paper with the attached striker. Whenever I typed two keys with adjacent strikers one after the other, the striker for the first key would be descending as the striker for the second key was ascending and they would jam against each other. I would have to reach in and separate them by hand.
Hence, QWERTY was designed so that letters commonly adjacent to each other in words were not adjacent to each other on the strikers. This left A, a very common letter, off on the far left to be typed with the little finger, which was the main complaint. That complaint is not important on a touch keyboard.
In college I learned to type punched cards on a keypunch. The letters and numbers were fixed in the QWERTY design, but all the other symbols, such as <, /, and }, were placed at the manufacturer's whim. This was extremely annoying for me, because when I switched to another keypunch, I had to search for the special symbols. The IBM keyboard standardized the location of those symbols later.
Software development instruction talks about making commands intuitive so that the users could understand them without reading the manual. We learned that intuitive usually meant resembling the previous system the users had used. Even a new system can feel like a non-intuitive change if a previous system became the unspoken standard.

Mathmuse |
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The key question is at time mark 2:20, "How do you make sure that the change is worth it for the audience as a whole?" Extra Credit's message is:
1. Demonstrate the value of the change to the user. This is best done through actions rather than words, because some players will embrace the change of a quest and spread the good news of the change to the other players.
2. Some changes affect all players yet are helpful only to a small subset of players. The developer must explain the need to the players who experience only the annoying side. And bundle it with another change that favors those annoyed players.
3. Some changes, often imposed by corporate overlords, are bad for everyone. Try to minimize harm while following orders and making the necessary changes.
4. Change is costly for the developers, too.
Pathfinder 2nd Edition has changes of types 2 and 3. The type 3 is the big one: by removing content tied to WotC's Open Gaming License, they protect their overall product.
The type 2 change is that Pathfinder is getting several new players. Therefore, Paizo sees a benefit for more material for beginners that they might as well bundle with the new content caused by the licensing problem.
How does Paizo minimize harm for the type 3 changes? They have to avoid disrupting the existing content. They cannot put red dragons into their new content, but they do not need to erase red dragons from anything already published with a non-revoked Open Gaming License. We players can eat our cake (the old content) and have it too (the new content).
This unfortunately means avoiding several changes that people are advocating, such as recent threads Errata Suggestion: Make basic rations worth 3.5 sp per week and Make previously uncommon ancestries common in new core rule books, that would override old rules and change the lore.
How does Paizo bundle good new changes with the bad new changes to keep us old players happy? When they remove old OGL dragons, they introduce new Paizo-invented dragons to fill the same encounter niches. They throw in a magic-tradition them to add more flavor. They remove the tiefling name and instead make versatile heritages even more versatile than before.

BigHatMarisa |

I will say that one big obstacle in attempting to keep "The Old Guard" (as much as I find those divisive terms distasteful) happy in Paizo's case is trying to tell people that the alignment they're so used to is now going to become an optional rule (as one example).
But, due to the short spaces with which Paizo has to talk about these changes AND the simultaneous need to not spill every single detail of the books, they don't tend to spend a lot of time with the "this is the compensation" aspects.
While I can only assume that the GM Core book will include Alignment as an optional rule - as currently running No Alignment is - I don't remember them ever confirming nor denying it? Despite the fact that it would make total sense to just swap the status of the two things, if people don't get a clear confirmation, all they'll hear is "Alignment Gone" with a vacuous hole left in it.
All they can say is "This is what we're changing" with only very little (if any) whys or hows, and that does make people nervous.

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The key question is at time mark 2:20, "How do you make sure that the change is worth it for the audience as a whole?" Extra Credit's message is:
1. Demonstrate the value of the change to the user. This is best done through actions rather than words, because some players will embrace the change of a quest and spread the good news of the change to the other players.
2. Some changes affect all players yet are helpful only to a small subset of players. The developer must explain the need to the players who experience only the annoying side. And bundle it with another change that favors those annoyed players.
3. Some changes, often imposed by corporate overlords, are bad for everyone. Try to minimize harm while following orders and making the necessary changes.
4. Change is costly for the developers, too.Pathfinder 2nd Edition has changes of types 2 and 3. The type 3 is the big one: by removing content tied to WotC's Open Gaming License, they protect their overall product.
The type 2 change is that Pathfinder is getting several new players. Therefore, Paizo sees a benefit for more material for beginners that they might as well bundle with the new content caused by the licensing problem.
How does Paizo minimize harm for the type 3 changes? They have to avoid disrupting the existing content. They cannot put red dragons into their new content, but they do not need to erase red dragons from anything already published with a non-revoked Open Gaming License. We players can eat our cake (the old content) and have it too (the new content).
This unfortunately means avoiding several changes that people are advocating, such as recent threads Errata Suggestion: Make basic rations worth 3.5 sp per week and Make previously uncommon ancestries common in new core rule books, that would override old rules and change the lore....
A post most excellent. Thank you, Mathmuse.

Ezekieru |

I will say that one big obstacle in attempting to keep "The Old Guard" (as much as I find those divisive terms distasteful) happy in Paizo's case is trying to tell people that the alignment they're so used to is now going to become an optional rule (as one example).
But, due to the short spaces with which Paizo has to talk about these changes AND the simultaneous need to not spill every single detail of the books, they don't tend to spend a lot of time with the "this is the compensation" aspects.
While I can only assume that the GM Core book will include Alignment as an optional rule - as currently running No Alignment is - I don't remember them ever confirming nor denying it? Despite the fact that it would make total sense to just swap the status of the two things, if people don't get a clear confirmation, all they'll hear is "Alignment Gone" with a vacuous hole left in it.
All they can say is "This is what we're changing" with only very little (if any) whys or hows, and that does make people nervous.
They've never once alluded to it being a GM Core optional rule. They made it clear it's a D&Dism, and thus it needed to be removed. It makes little sense to remove it for legal purposes and establish their own identity better, only to put it back in as an optional rule in the GM Core.

HumbleGamer |
1. Demonstrate the value of the change to the user. This is best done through actions rather than words, because some players will embrace the change of a quest and spread the good news of the change to the other players.
Point 1 is what I always consider to be the best ( demonstrate the value, but not only towards changes, but also towards brand new features ).
Having done this since day one would not only have contributed in sharing paizo pov / intent with 2e mechanics ( getting closer to the community ), but it would also have helped clarifying ambiguous rules, leaving no room for interpretation at least for what concern major issues.
I know it's something that requires time as well as an agreement on how the whole package works ( which might not be always easy ).
This unfortunately means avoiding several changes that people are advocating, such as recent threads Errata Suggestion: Make basic rations worth 3.5 sp per week and Make previously uncommon ancestries common in new core rule books, that would override old rules and change the lore....
That might be true to a point.
Being almost/around 4 years since 2019, I think it requires not so much effort to understand what are the priorities for players ( just by lurking reddit, for example ). Obviously, this would probably exclude last minute requests ( back to your examples, it's the first time I read something about splitting the rations price ), but it woudln't be a big deal.
ps: I too agree with what you wrote about point 2 and 3, for this errata.