u/EconomyCounty4064

Is it worth filling in the weathered window trim with wood filler? If so, what wood filler would be best?

The exterior window sills on my house are all caulked underneath, but the caulk on this one had failed and was separated so I cut off the old caulk. Should this gap be caulked and sealed again? Otherwise if it is supposed to be open, should I remove the caulk underneath on all my other window sills? The house was built in 1900 and the siding is aluminum

My house was built in 1900 and I am repainting my exterior window trim for the first time since purchasing the home 6 years ago. At the top of each window is a piece of crown molding with a piece of flashing on the top of it and a piece of flashing on each side in the shape of the crown molding. The siding on the house is aluminum. Do the edges of all the flashing need to be sealed/caulked to the trim & siding?