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Attempt 2 was a disaster. Wiped to a trainer I accidentally walked in front of while coming out of Silent Hills with my team in a really bad shape. Couldn't stand a chance.
Attempt 3 (with Chikorita) didn't go much further. Wiped to a sage in Brass Tower who had the perfect counters to my team.
Now trying again with attempt 4, starting with Palssio. Team looks promising and I gotta grind it well to avoid surprises.