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Up to you how you prefer doing it. You may find that some paints don't like some caulks. For that reason, I caulk first. I've used primer over caulk where the particular paint has been fussy (some will craze). Ignore the 1hr or whatever it says on the tube for drying as your water-based paints will lift it off unless you let it properly set.
rodabod
LongAndWinding
Yay! Part of my novice plan... got the required stuff, had a dispenser. Was first going to sugar soap skirting/doors once electrician is done chasing the wires in, then undercoat walls/skirting before caulking gaps. Have seen varying preferences for decorating, start from top, skirting first, skirting last ...