I posted this in the Reddit forum and made some progress. Posting here both to see if there are other approaches and to let others know of a workaround.
Strengthening holes is common whether for installing threaded inserts or simply carrying the load of a fastener. Common but seemingly hard to do. You can increase the whole print wall thickness but that wastes time and filament, especially for large objects.
Using modifiers sucks for this. Manually drawing, sizing. positioning and then maintaining cylindrical modifiers is tedious and error-prone. Larger modifiers (e.g., cubes) don’t behave well as they seem to insert walls to match their shape and so weaken the overall structure and cause surface anomalies. See the pic below (that square in the middle is the modifier. See how it added walls where there shouldn’t be any!)
I think a modifier that acts simply as a “selection region” and applies its modifications in that region is the “right” answer but the software doesn’t work that way currently.
Watching https://www.youtube.com/watch?v=WPNANe5pRsQ inspired the idea of adding extra thickness directly in the model. Essentially add embedded “hole liner” parts and print them together having tweaked their strength settings. This makes it easier to maintain the liner thickness, length, position, … but can cause some funky artifacts (as shown in the video) and means that your designed object has the liners as part of its definition.
Talking with Martin_SV on Reddit a tweak to this came up where you draw the “hole liners” in addition to your part, export them together in a separate file, and then Load them as a modifier and tweak their settings as desired. Based on my initial test this seems to eliminate the funky bits of the video approach while retaining maintainability, ease of sizing and positioning, and the integrity of the part design.
Not the ideal answer but it seems like the best we can do with the current software. Hopefully I’ve missed something and it’s even easier. If not, hopefully this helps folks.
