Suggestions for make this "fine" woodwork a little cleaner?

I'm installing shutters. When I got into it I realized the windows needed overall attention attention (painted shut upper sash, no weather stripping, 6 coats of paint on everything. So, made it a whole rehab, strip the paint from every surface, replace the cords with brass chain, weather strip etc.

I see lots of air between surface meets. Any suggestions for remedying the current state and avoiding it when I get to that step on the other two windows?

More information&pix (aka my ramble)...

Suggestions for make this "fine" woodwork a little cleaner?