From my understanding, and this was well before my time, resolving exactly these kinds of trademark issues (including the ability to use “State of the Map” for its conferences) was one of the major reasons that OpenStreetMap US chose to become a local chapter.
It is also one of the reasons that independent projects affiliate with a LC, like OSM US’s charter and community projects. There is a family of local chapters and affiliated projects that all use the OSM marks with the formal permission that comes with that affiliation. This is a good thing.
I used OSM US as an example that I’m familiar with, but other local chapters have affiliated projects as well.
OSMF exists to support the project. It does that by running the servers, forming local chapters, protecting intellectual property, running conferences, and generating goodwill.
Running a hyper aggressive legal campaign around trademark protection is something that OSMF could do, but as with all tradeoffs it comes at the expense of other priorities and focus areas. Personally I’m happy with the approach of the LWG engaging with projects and asking politely.
More aggressive enforcement should be reserved for more flagrant violations. That is why I’m calling on @NorthCrab to do the right thing and show us that he’s community focused and not just running a vanity spite project.