Originally posted by Bermejo
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Small pots will dry out fast. If you're watering from the bottom then you need to be careful how long you leave the pots standing in water or they'll get too wet - not everything likes wet feet.
What medium are you potting in? Some things look/feel dry even when they're perfectly fine and others drain well enough that even if they seem wet it's not an issue.
I really think it's mostly trial and error. Humidity, temperature, potting medium, air circulation, pot size, etc all play a part. I usually start mine off in a coir/perlite mix but last time I bought vermiculite and just that one change means I have to water differently.
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