• 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.

  • I was thinking more about how it can be tough to get the water to reach all of the compost sometimes in a large pot

  • Well it kinda depends on how big a pot you're talking about, but what you'd ideally want to do is have a big bowl / tray / container with water that has been sitting in it for a while, with a water level somewhat below the height of your pot(s), and then you put the chili plants in there and let them soak up the water.
    That way you don't flush any nutrients out of the soil and give it a chance to soak up nicely.
    If that's not an option I usually give them just a little bit of water first (which will "open up" the dry soil) and then a big gulp an hour or so later..

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