I love to caulk! (kind of goofy, I know). My favorite is the one annz mentioned, DAP Alex Plus tube looks like this. And ditto the good caulk gun. Splurge and spend about $12 on a contractor grade (Home Depot has them in orange, I think they are red at Lowe's). It makes all the difference. Softer grip, smooth squeeze application versus the hard uncomfortable grip, jerky movement of the couple dollar guns. Just be sure you're not filling large gaps (it will say on the tube the max size). I generally keep a big solo cup with me (those 10 oz + 'party' size), a little bit of water in it. And a clean damp, but not dripping lint free rag. Rarely use any smoothing tools, just light pressure with my finger (you can wear rubber gloves as long as they're snug). Keep dipping finger or smoothing tool in water, shake drips off, and it helps. Then any excess caulk on my finger after smoothing I just wipe on the rim of the cup. Sometimes it fall down in the cup, if I get too many blobs in the cup I start with a fresh one. It's tempting to use harder pressure, but all that does is just squish it out on the sides, then you have a funky raised edge. Light 'n smooth. ;) Oh, and little drops will happen (maybe onto the floor). Best thing to do is just let it dry and it pulls up on one solid piece. Try to wipe it when fresh and it will make a big mess. (To avoid blobs or caulk coming out gun when I'm done, I release the pressure on the gun about 3" or so from my end point. Caulk will still come out. The reason it seems like your bath caulk never cured is because it's all silicone (rubbery texture when dry). I don't like working with that stuff, it's a gooey mess. But some areas, like kitchens and baths where water is involved, it's the better choice.

I've always painted the rims when I've painted the ceiling. I like them to blend in. I find the lenses make the light too dim and stick with the bare bulbs. I only use 5 recessed fixtures in the new space, supplementing with pendants, a fluorescent center fixture, undercab lites & another ceiling light, so I'll be able to minimize using the cans.

These comments are all very helpful. Thank you. While you were writing these comments, we were meeting with a contractor who is going to address some omissions with the board and batten siding and flashing. He too, concluded that fixing it with pieces of mahogany would be best. I like the idea of the caulk for deep voids as well. We have some leftover trim from the door install (pieces that are are different than the casing). I will go and see this base trim and see if we can fashion some from what we have leftover. Todd -- LOL. I think you are correct that we will never see the mason again as he has been paid in full.

Correct, Hallet & Co., those are the areas that can be painted. To clarify, you are suggesting to paint all trim, corner boards and pergola white. We are keeping the entry path as concrete, but adding a flagstone path through the "garden" to the side gate. It is a darker flagstone. You are suggesting darker stucco in the same family of SW Kilim Beige (putty color) to ground the house? Do you agree garage door should be same color as the stucco? I'll look into taking the knuckles off of the railing. What "look" would you say you are you going for overall? Thank you!