So I don't see this as bashing Gygax, but perhaps damning him for too much intentionality... My impression is that OD&D (or the LBBs) at least are themselves an aggregate work. A combination of Arneson (and those he was influenced by) and Gygax working across a few months or a year of rapidly evolving games. If one looks at OD&D in the way you'd look at an old OSR blog discussing the author's campaign, house rules and development ... I think it fits better.
Where praise is owed is in the creativity and the willingness to explore something new. The actual LBBs aren't entirely coherent ... though some parts are in very good ways. The Dungeon section of Dungeons & Wilderness adventures is solid, but it also feels pretty contradictory to the wilderness part and the tables in Monsters and Treasures (including adding very brief rules for smaller in dungeon treasures and encounters.)
To me the genius of OD&D is that it has some very good compromises (flat damage and HD, limited AC, good rules on dungeon turns and light usage) that make for a fairly flat power curve and solid basis for dungeon exploration. It's implied setting is incredibly influential, but doesn't stand the test of time in the same way ... and it need not. OD&D invites the reader and referee to contextualize it in their own ways, and I love this.
The problem is that at no point does it actually tell the reader that the Wilderness encounter section assume its only the true wild, nor does it tell you what to do if your starting location was, say, on the fringe of settlement and had true wilderness at one edge but at least semi-settled areas on the other. The Wilderness encounters were going to be bizarre failures for the latter, but there was no discussion of what you should do instead.
Its all fine to say "GMs need to work that out themselves," but at that point it behooves the designer to
say that, and ideally give some idea what things they need to do rather than just hope they wander into the deep end themselves and don't drown.
As you say, the contrast with the discussion of dungeon exploration is striking; one can argue a certain degree of unexamined stylization is present there, but its at least set up with the idea the end user is going to probably need tools and guidance about how to go about it, in a way the outdoor section isn't.
As I said,, part of the problem with the Wilderness encounter material is that it requires a particular approach and set-up to be survivable
at all and I suspect all too many people using the game learned that the hard way.
(You can argue town/city adventuring is even more poorly supported in OD&D, but it at least doesn't have a section that can be read as being about that while only being really about a subset of it at best)
