re: Simple things you can’t seem to do right

For a true joint sealant with backer rod (not painters caulk or similar). You push the bead into the joint rather than pulling it across it. Clean the tip often with a rag soaked in xylene, and tool the bead with a professional caulk tool (coated and cleaned with xylene).

For painters caulk you can just about do anything and get away with it- other than make the tube explode