Help with sash window

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Hi, I'm sanding and repainting my sash windows in only 3 weeks (scaffolding time constraints). So many layers of paint on them... it's horrific!. Whilst I know I'm doing a patch job due to time and money, I wonder if someone could advise me on what to fill the gap between the outside beading and the masonry? I have gauged out the flexible filler between the bottom of the window and the sandstone cill and wondered if I should put a flexible filler back in? I'd like to paint the filler to match the widnow. Lastly! I have horrible plastic black paint on the sandstone cill. Any advice how to get it off? thank you
 

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Careful there maybe lead in paint.
Fill with 2 pack wood filler.
Then a polymer mastic over.

Better stuff to use would be repair care resin.
 
Thank you so much. I've looked up these products and I guess the Repair Care resin would be better as it's both flexible and I can paint it? I am using a respirator mask, glasses and gloves so hope I'm avoiding any dust.
 
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