Caulking: If it feels like you're about to screw up, back it up a titch and then keep going. It's always easier to remove a bump than to fill in low spots (which, actually, is impossible).
Also use top quality silicone. I like GE brand. If it's falling apart every year you used latex caulking, which is totally and utterly useless. And make sure it's meant for the area you're caulking.
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