Re: caulking sideboards
For exterior work that will receive a lot of direct sunlight or expansion/contraction due to temp fluctuations, I would recommend a poly/beutyl type caulk.
It's best to work in cooler temps so that the caulk doesn't skin over before you can get it applied and laid off. I would suggest mornings or later evenings when the temps are cooler, also, pay attention to how the caulk is responding to the heat. If it's skinning over quickly, then run shorter beads that you can get laid off and finished before skinning occurs.
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