The hardest one might be the Regular Season of DD Season because we don't know how many wins that requires.
The one that takes the longest will be the 5 strongholds in Conquest.
Most expensive will be the 5 equipment Tiers(unless you get lucky and pull a Diamond Equipment somewhere)
Then the Same Name one is easy to accomplish with some roster editing, in a stretch of the year you'll get a lot of opportunities to strike out and then hit a home run next atbat with that guy.
All the other stuff can get done the first day of the game or at least the first week.
The only trophy I didn't get last year was the 20 wins in BR and I platinumed 2 years ago.
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