Confused about painting window frames

Hi all,

I have begun the rather large job of scraping back and repainting the outside window frames and sills on my old weatherboard place. The original paint has pretty much peeled off exposing the bare wood and there are some areas of rot in the corners which I intend to fill with bog (would this be the best thing to use or should I use a paintable silicone). Much of the old putty has come out from between the window and the sill and it has left a 5mm gap. This I intend to fill with paintable silicon unless I should be using something else like putty itself.

My real question is when I should use the putty or silicone. Should I apply a layer of the paint I intend to use (I have been recommended an all in one paint from Bristol) and then fill the gaps with silicone or should I fill first and then paint over it. The surface is a mixture of old paint and bare wood.

I'd love to hear some answers and opinions and many thanks for any that come in.


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