How can I avoid a jumbled mess as shown above without having to manually fix it in edit mode or use Clamp Overlap in the Bevel settings?
Start from a plane with evenly distributed vertices and faces filled around the number 2. Then select all faces and press I to
Inset Faces as deep as possible, don't mind the intersection as we will tackle that after. Press NumPad-7 to go into Top View and just manually do a combination of moving, creating, deleting, and dissolving of vertices to make the faces distribute somewhat evenly and fill new quads. It doesn't have to be perfect. Then make sure you have no overlapping vertices by selecting everything with A then press M > Merge By Distance. And then you can easily Bevel the Edge Loop nicely with Ctrl+B.