I'm gonna try to write a simple walthrough which trainers to fight after we collected all the mushrooms after the 1st Leo Fight:
This guy right before the path towards City Road:
This guy inside the Gym in Big City:
After both these easy fights, you should have a lvl 20 Cap
We can continue fighting some more trainers inside Big City, both have 2x lvl 15 mons.
One is a male officer near the first guy we beat, the other is a man sitting on a bench near the south exit towards Cave Road.
Then we fight the guy sitting on the bench before the big Department Store who has a lvl 16 and a lvl 18 mons.
This puts the cap at lvl 23.
From here, you can optionally start the Teahouse event on Beach Road.
This leads to another easy fight, but you can also save this for later until you beat Maki if you want to see a small Easter Egg of a slightly altered quote from her. (1 lvl difference is very small).
Beat the Monk (lvl 20) and the Nun (lvl 21) on Holy Road.
Then look around for trainers inside the Gym, City Road, Beach Road, Harbor town, the Ranch and any previous trainer we skipped that are now within your lvl. to beat.
Eventually you start to snowball and reach a cap of lvl 40-50+ as you start clearing every trainer in those areas.
Then after the Central Event where you meet Athena, there are some trainers to beat in your home town (a girl in front of your house and a ninja in the topright corner) and the cave that leads to Wano Village and you can keep snowballing until you are strong enough to beat Star Trainers.
This guy right before the path towards City Road:

This guy inside the Gym in Big City:

After both these easy fights, you should have a lvl 20 Cap
We can continue fighting some more trainers inside Big City, both have 2x lvl 15 mons.
One is a male officer near the first guy we beat, the other is a man sitting on a bench near the south exit towards Cave Road.
Then we fight the guy sitting on the bench before the big Department Store who has a lvl 16 and a lvl 18 mons.

This puts the cap at lvl 23.
From here, you can optionally start the Teahouse event on Beach Road.
This leads to another easy fight, but you can also save this for later until you beat Maki if you want to see a small Easter Egg of a slightly altered quote from her. (1 lvl difference is very small).
Beat the Monk (lvl 20) and the Nun (lvl 21) on Holy Road.
Then look around for trainers inside the Gym, City Road, Beach Road, Harbor town, the Ranch and any previous trainer we skipped that are now within your lvl. to beat.
Eventually you start to snowball and reach a cap of lvl 40-50+ as you start clearing every trainer in those areas.
Then after the Central Event where you meet Athena, there are some trainers to beat in your home town (a girl in front of your house and a ninja in the topright corner) and the cave that leads to Wano Village and you can keep snowballing until you are strong enough to beat Star Trainers.
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