Bleap
The only criticism is that even after decades of medieval bloodshed, he should still have an "impression" of good guys and bad guys for the major characters of the 5th HGW if he was ever exposed to FSN in his original life. Well, either way as an author your scene writing and dialogue seem pretty solid so the story is still solid enough. I just hope he doesn't go too blind as the 5th HGW happens, otherwise it would really make his origin as a transmigrator almost completely superfluous.