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I only have one digital drawing device, a tablet that I have sitting around somewhere and never really bother to pull out because I virtually never do the sort of freehand stuff that it'd be useful for. It is some no-name brand, and doesn't have tilt sensitivity, a virtual eraser, or more mouse buttons on the stylus. Since as far as I can recall, Wacom's kinda been the leader, and if someone was going to be doing serious freehand artwork, I suspect that that's probably where I'd recommend going.
My favorite drawing software would depend a very great deal on what the task is.
Natural-media
I used to be interested in watercolor simulation, read research papers on it. I have not been blown away by what software I've seen that tries to simulate the physical interactions of watercolor paint has managed to do. Less interested in simulation of ink drawings, but I've played with natural-media software that tries to simulate it. Again, not blown away.
In 2025, if I wanted to make something that looked like a watercolor or most other forms of natural media, I'd probably use a generative AI, maybe start with an image and rely on the generative AI to simulate the natural media effect. I don't think that computer simulations of natural-media painting or ink that I've seen are as effective.
If I were required to do it freehand myself, given that I don't have any proprietary Windows natural-media digital painting software sitting around and last I looked
a very long time ago
that was probably the most-sophisticated, I'd probably use Krita. I generally prefer Gimp for image manipulation stuff, but Krita has, as I recall, more natural-media stuff.
goes looking for an example of someone using natural-media stuff in Krita
Pretty much anything else done by hand and raster
Gimp.
Vector, freehand or manually-placed elements
Inkscape. I've never done anything meaningful freehand in it, though, and never used a tablet with it, so I have no idea what support is like. I imagine that it probably can generate paths with variable-width depending upon tilt and pressure and stuff, though. I've used it to lay out vector graphics with a mouse, and it's been fine for what it is.
Example Inkscape gallery
Vector, technical 3D stuff
Blender, if it wasn't something intended for the actual real world. Looks like Blender can generate isometric technical drawings.
I've never used FreeCAD to generate technical drawings, but I'd bet that it can do the above. It can do parametric modeling, probably more useful for modeling things where you actually care about the model representing something that's gonna be in the real world. I bet it can do cutaway views and stuff too.
investigates
Yeah:
Though they recommend other 2D CAD packages if you don't need 3D support:
Vector, generating from code
Maybe MetaPost. It's been a long time since I've used it. Maybe Asymptote. I've used both, most-recently to generate vector images of optical illusions.
For 3D stuff, I've used OpenSCAD much more recently to procedurally generate 3D objects to be created by a 3D printer. Doesn't look like it can generate technical drawings akin to the above CAD packages, though. I guess that you could probably model something in it, then import it as STL to FreeCAD and use that to render a technical drawing, though.
EDIT: You didn't specify a platform. Everything above runs on Linux, and is free and open-source. Probably most of it can also be used on other PC platforms, like Windows and MacOS. If you're talking Android or something, different ballgame.
EDIT2: Oh, yeah. Kind of stretching the limits of "drawing", but if I were doing some kind of graphic visualization using code generated from a large dataset, I'd use R, which is something that I've been trying to play around with more for the past few years. Like, if you had to generate the kind of data visualizations that the New York Times or someone has to put up quickly, that's the sort of thing that you'd want, and it can do a lot; being able to suck in a lot of data, massage it, and spit out something is useful for maps, charts, and infographics. Stuff like this: