Hi Totally, Thanks for the pic as that helps. Beautiful home! There looks to be quite a few entry points that are possible. Earlier you stated that the caulking is gone around some of the windows noticed by the roofer. Even though you dont want to solely rely on caulking, it could be that the lack of is letting water in at a point probably around the sill area of the window,(the outside stool), and running in where it is penetrating likely due to improper flashing. Caulking can keep rain water away and from running in, but the importance of flashing is to keep moisture, such as condensation, from collecting around areas and seeping, which is in a way worse because it goes unnoticed for quite some time leading to wood rot, mold, ruined insulation, etc. If there is a positive to your dilemma is that you are able to actually see that you have a problem and address it. With the window type you have, brick will have to be pulled to get to the perimeter and flashing.The possibilities other than the lack of caulking could be at the upper gable above the window where water is running down behind where the siding meets the gabled roof line, which would most likely be a flashing problem as well. You might want to have that area checked , but my speculation is that the rain was getting in that uncaulked area and was able to get inside the wall cavatie through bad flashing. Even though some of the other windows are un caulked, it could just be the way the rain water traveled and was able to penetrate that particular window, especially with wind driven rains. Some possible links to people who could inspect could be a siding/window outfit, a home inspector, or a contractor. Your roofers could be considered as well as they are experienced w/ flashing concerns. If it is determined that brick should be pulled, i would get a mason for the removal and replacement. Hoping it all works out soon for you and once again, beautiful home!

I don't think it will look weird; we have that set up in our house. Our window trim is fairly developed but our interior doors just have basic trim. The exterior doors - like our french doors and front door - do match our window trim, however. The previous owners did the trim so I'm not sure what their methodology was, but I like it!

The finger joints frequently telegraph through the paint and become visible in a year or five. It probably depends somewhat on just how evenly the wood was dried prior to fabrication, but also on small variation in seasonal movement from piece to piece of wood from different trees. The former can be solved by acclimating the wood to the house and sanding it even prior to finishing, the latter can't. Something to bear in mind-- if that's going to bother you, upgrading to poplar will solve the problem.

A picture of the whole room is what I would need to see. Are you planning drapes or what kind of window covering? I don’t think it would look right to paint the trim like the walls in fact I think the baseboards and the trim could be wider.