I would sometimes fold preflop and sometimes raise the flop depending on the player, so I don't think there's much point in discussing that.
Not betting the turn here is really bad, he may very well call two streets with QQ/KK as is the tendency of donks and you're not really hiding the strength of your hand by checking the turn (looks like pair which plans on calling any river bet). You also lose value if something like a
rivers or get drawn out yourself.
*EDITED: Flatting flop = checking the turn
The better player should win the race. Always.