DB, If I had to hazard a guess, I'd say your photo was taken somewhere between about Olene and Dairy, and probably no farther "east" than about Hildebrand. Nice catch, glad you were there... it was, evidently, a fascinating operation. I lived in the area for a number of years and hiked/biked/snowshoed/drove pretty much the entire OC&E trail, as well as the Woods Line, and many of the associated spurs.

RE the timber growth, it's spotty. Some areas have re-grown fairly nicely, others are quite barren, either due to subsequent fires, or simply due to poor growing conditions. The early loggers, followed later by the USFS, Weyerhaeuser et al really didn't understand, initially, how fickle and slow-growing some of these east-side pine forests were... and by the time they did figure it out, they didn't really care if/when the timber grew back.

The big Bootleg fire of 2021 burned a lot of timberland adjacent to the Woods Line; I drove through the area last fall and spent a day or so hacking around in the forest in that area. Some areas got totally nuked while others were untouched, and everything in-between. There was some salvage logging going on.