For seedlings I like to start my soil ones in peat pots so when the root tips creep out I transplant them into bigger pots.
For Peat its easy to water, cause the pot gets wet, then when the medium is mostly dry the pot is also dry. Pretty simple, water til peat is staturated, then when dry complete re-water.
For bigger pots, everyone is different, I prefer to leave a 1in. ring between the top of the pot and top of the soil, I then flood the pot up to ring as quick as possible and let it drain down, most even water spread. Now some people will do this til about 15-20% of pot volume is in the catch pan ( which is discarded immediatly btw ) then leave without watering for 2-3 days with my happy frog mix up to 5 days.
I prefer to water more often so I will do 1 or 2 runs, which should cover about double the distance from soil to rim very well but moisten everything aight allowing me to feed / water a tad more often. With this and taller narrower pots is compacting of the lower soil, or because its so far down doesnt dry out as quickly specially with no roots, then you end up with nasty mushy moist almost rotten soil down there which is no bueno.