Gallery asked for more work "in the same vein", how far did you bend?
Years ago a dealer told me my still lifes sold and asked if I could "stay in that corner" for the next show. I did it. Painted eight of them, sold five, and by the sixth I felt like I was copying myself badly. I never went back to that gallery.
So: what did a gallery ask you to change, and did you? I want the honest answers, including the ones where you said yes and it worked out fine. Tell me I'm wrong if you think you should just take the money and paint your own things on the side.
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The part that catches me is "by the sixth I felt like I was copying myself badly." That is the real cost, not the money question. In printmaking I live with repetition by design, the whole point of a multiple is that the image survives being made again. But there is a difference between repeating a matrix and repeating yourself because a room full of buyers wants the same thing. The second one hollows out fast.
I don't think you were wrong to say yes once. A dealer saying "these sold" is information, not a command, and eight paintings is a cheap way to find out what you actually think about the corner. What I would push back on is the "paint your own things on the side" part. For me that never works, the side work becomes the real work and the sold work becomes a job with a signature on it, and eventually the two contaminate each other. I would rather negotiate the vein than split myself in two. Same family of concerns, different door.
So no, I don't think you should have just taken the money. But I also don't think one show in the corner is a betrayal of anything. It is a test.
The "information, not a command" line is what I needed to hear honestly. I've never had a gallery ask me for anything, but I have caught myself painting what did well at a fair instead of what I actually wanted to paint, and it sneaks up on you. Eight paintings does sound like a cheap way to find out, though I bet it didn't feel cheap at number six. Did the repetition teach you anything you kept, or was it mostly just a lesson in what not to do?
The matrix comparison is the right one, and it clarifies something I hadn't put into words. A plate can be printed again because the plate is the work, not the effort. Painting the same still life eight times isn't repeating a matrix, it's repeating a decision I already made and can no longer remember making. That's where it goes hollow.
And yes to "cheap way to find out what you think." Eight paintings taught me more about my own limits than any amount of thinking did. I just wish the lesson had cost me five canvases instead of eight.