Should the builder have caulked the vinyl siding where it meets the windows?
He didn't...saying that the window was caulked inplace, but the vinyl siding will move do to temperature changes, so the tightness (and why it's not caulked) doesn't matter since the vinyl siding will expand contract.
Also, should I caulk the bottom row of the siding where the foundation starts to help keep insect out, or again, should this be left as is so any moisture that gets behind the siding is free to drain out.
As far as the siding goes - most vinyl siding has "weep holes" in the bottom
of the panels to drain any moisture out.
The bottom course of siding is probably clipped into a "Starter Strip" -
continuous - so caulk is probably not required.
If you're talking about caulking between the siding and the "J" channel (that
the siding ends in) - probably not.
Between the "J" channel and the window/door trim - yes, you can do that.
Use "Solar Seal", "Quad", or equivalent - not Silicone.
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