If the water dribbles out the holes, that means that you've fully watered them, which is good. It's only a problem if the mix retains too much water (see above comment re: PWT). If you stop watering before water comes out the holes, there's no way to know how wet the soil is. If you have a proper mix and proper drainage, you can't really overwater.
As for fertilizer, I never have been able to find much of a good answer as to "how much". I use only liquid ferts after plant-out. I think, in a well-draining mix, it would be hard to over-fertilize. The best thing is probably to go easy and go slow, and see how the plants respond. You can read the FAQs from Texas Tomato Food (somewhere... a thread here?) that discuss how/when to fertilize using their product, which I think is relevant for all liquid ferts.
Good luck!
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