There is no one-size-fits-all answer, indeed, I have used 2 or 3 different irons/tips on a single board, depending upon the PCB involved.? Smaller pins/components with tighter spacing need a smaller, perhaps conical tip, whereas a larger, ground pin or TO-220 part may need a larger chisel type at a higher temperature.? You may need yet a third to solder large power conductors or RF connectors.?
I have 3 soldering stations and many different tips on my assembly bench and I have had them all in play on a single project.
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One thing which will help is the application of background heat to the board; it will make soldering much easier and is actually less stressful to chip components as the board and components cool and contract.? Even putting it onto a 100°C hot plate helps immensely.
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73, Don N2VGU
Donald S Brant Jr