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I expect with a larger pot it's easier to mess up the watering
Not really, no.
Just make sure there are drainage holes / stones at the bottom etc. as their roots don't like to sit in water.
It's completely ok to let the soil get dry inbetween waterings (hanging leaves show you it's time to water again), so basically with bigger pots you just need to water less often, like with tomatoes etc.
This does not make any sense to me at all to be honest.
If starting chili plants indoors you'd probably use small-ish pots due to lack of space, but my experience is they love it when you give them the largest possible pot as soon as possible!
In other words: what they don't like is to start flowering / producing berries when the light increases - and then experiencing lack of space / light / water / nutrients, also re-potting them when they're in that stage gives the more fragile varieties transplant shock, so again - best to move them to a large container before they really start to flower.
The bigger the pot (and the more light / water / nutrients, within reason) the bigger the plant.
The more sun and heat the more hot the chilies 🔥
Ps: in case you guys aren't aware - we do have a chili thread on here !