Window Frames and Sills on Older Carlsbad Cottages

The soft give of a thumb pressed into a window sill is the first thing every house painting teardown that carlsbad house painters black forest meadery has logged on an older cottage turns up. A 1950s bungalow in Olde Carlsbad or The Barrio in Carlsbad, CA often has wood frames with decades of paint layers, and the sill takes the worst of the water.
Where the wood fails first

The sill sits flat, so water pools on it, and the joint between the sill and the frame lets it into the wood. Soft spots show up at the lower corners of the frame and under the glass. Probing with a screwdriver tells more than a look, and rot that goes deeper than a thumbnail is cut out and rebuilt, not painted.
Repairs before paint

Small soft areas get consolidated and filled with an exterior wood filler, and bigger sections get a spliced in piece of new wood. Cracked glazing putty is dug out and replaced, since a failed putty line lets water behind the glass. Patching and spackle on interior returns come after the exterior is sound, and sanding follows each repair until it is flush.
Old paint layers
Homes this old can carry several coats of oil based paint, and lead was common in paint made before the late 1970s. A test kit tells whether it is present, and if it is, wet scraping and wet sanding keep dust down. A scuff sand on sound edges is fine, but heavy dry sanding on unknown paint is not.
Caulk, primer and masking glass
Bare wood takes primer, and the joints between the trim and the wall get a flexible caulk once the primer is dry. Masking the glass with a thin tape line, or cutting in with a steady brush a hair onto the glass, seals the edge so water cannot creep behind the paint. Two coats of satin or semi gloss enamel finish the frame. Painting the sill with a slight slope for runoff, and keeping paint off the sash edges that slide, keeps the window working.
Shutters
Louvered shutters are best taken off the wall and laid flat, then painted on both sides and the edges. A sprayer gets paint into the slats faster than a brush and a roller does, though a brush finishes the fine edges. Hinges and pins should be wire brushed or replaced while the shutters are down, and the screws checked for rust before they go back up.