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It's all good saying that, but it's very difficult for a small team to balance working for new players vs. working for old players. Let's say for example we discover that there is a big dropout of players at the tutorial and we assume that the tutorial needs to be redone. The time it takes to redo the tutorial results in the existing players not getting new content, then when the tutorial is replaced people are like "wtf?" because it's not something that benefits them.
The same thing applies when it comes to holiday content. You're damned if you don't and you're damned if you do.
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Month 1: New player update
Month 2: Current player update
Month 3: Old player + Current player update.
Repeat. Example, not saying it takes 1 month, before you post about it.
Damned if you don't, damned if you do? Well then ask the players what they want first... give them an example of how long things could take, even if "we don't tell players what we are planning, because Supplies"