This is sort of a companion thread to this one about iPad pixel art apps, but I'm wondering if someone can help point me towards a good app for doing monochrome pixel art on macOS.
The big feature I'm looking for is something that feels very basic, because it was in every paint app for classic Macintosh, which is the ability to paint pixel-by-pixel using a particular 8x8 pixel pattern.
I've tried at least 10 different pixel art apps for the mac (and a few for Windows too), and none of them have this feature! The two closest I found was Aseprite, which allows creating custom brushes from pixels in your image, but it doesn't let you paint pixel-by-pixel. If your pattern is, for example, 4x4 or 8x8, then it only lets you paint with brushes that are 4x4 or 8x8. As near as I can tell, there's no way to paint the pattern one pixel at a time. I'll give an honorable mention to Pixen, because they specifically added features to their app for doing Playdate graphics. But similar to Aseprite, they don't have this feature for painting patterns pixel-by-pixel (there's a tongue twister for you). It only allows tiling a pattern.
Is there anything better than running an old Macintosh painting app in an emulator?
I still use Classic Macintosh apps. And I maintain a list of Japanese pixel art apps from the past 40 years. And I've done extensive research into non-Japanese apps. Not many of them have the "draw with pattern as ink" feature, and most of them no longer work on modern systems, but one is all we need:
Here's the pattern editor (double-click any pattern to edit) they are saved globally with the app, not with the document.
Piskel
Also, I maintain a desktop fork of Piskel to which I've added Playdate-specific features (image table import) and other new and additional features, improvements, fixes. But it doesn't have the feature you want. Though you can draw in dither patterns of 25%, 50%, 75% (and 100% and 0% obviously). And it has toggle pen!
And finally I created an extension for Figma to allow me to create vector art with pixel fill patterns. That's how I do my 1-bit teaser art. Not quite what you want, but close, though sadly I have no plans to release this publicly. But it might give you some ideas what is possible.
I've split AzPainterB out with its own screenshot.
I asked the Japanese user who published the AzPainter3 tap and they were kind enough to publish a tap for AzPainterB!
Other apps
Also, worth mentioning that you can wrestle this behaviour out of many other apps (Photoshop, Paint Tool SAI) by using layer and draw modes, something like:
Create a pattern that takes up the entire canvas
Set it to black
Block transparency
Set the layer mode to lighter colour
Anything you draw will come through as the pattern. I don't personally do this, but I know this would be light work for heavy Photoshop users.