Hmm, proud is a weird word for me for achievements. Usually do it more to challenge myself and if I can go the extra step in my favorite games. I've gotten a few achievements and trophies. Not all challenging, some just because the games are really enjoyable_
Akumu mode in TEW is usually considered one of the hardest ones of the current generation of games I guess; though at this point I've done it eleven times.
Honor Mode achievement in D:OSII is also in the 0.3% scope of achieving. Though huge RPGs I imagine most beat once then dive into Game Master Mode. What makes Honor mode interesting is the game isn't exactly easy, can at times be cheap, add tactical difficulty and a lone save slot that deletes itself if the party is wiped. So require a perfect playthrough. Note that D:OSII isn't exactly a short game.
My last platinum was Bloodstained: Ritual of the Night. Though wasn't challenging. The game was fun and was what I would call an easy platinum trophy. Just like SotN. Beating the CastleVania classics was harder, but I'm sure most either cheesed them using passwords or save-states. Which diminishes the experience honestly, wish they didn't add them-in but that's just me. .
*Probably have more but Akumu and Honor are likely considered the most overall challenging. Based on difficulty.
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