It depends on the species of wood (I.e. How hard or soft) and whether or not the ambient temperature can remain as stable as possible. What you caulk and paint in warmer weather may look great now, but when it begins to get colder, the wood begins to shrink, and the caulk will begin to pull away. This will look worse than if you didn't caulk at all. My suggestion is to use a caulk like the brand called "Big Stretch " in an attempt to avoid this.

I recently saw this episode of Ask This Old House where they demonstrated painting tiles - especially as a solution to get one through till an entire redo is possible. http://www.thisoldhouse.com/toh/tv/ask-toh/video/0,,20902001,00.html Looks like you are doing a great job!

Hi there, has anyone painted clinker brick before? We are looking to update the bricks by painting them white and recladding the second story in cedar. Advice welcome

Swimming pool season is upon us, rather late I might add this year, you may be considering painting your pool. There are a few things to consider is what the previous coating is and the appropriate preparation that is required. When we quote pools we generally only get to inspect them with water in them. We will always put a clause in to assess what the actual condition is like when empty, like when we found a good portion of the surface was very drummy and subsequently we had to remove a lot the surface and replanted, always be mindful of hidden costs when pool painting, they are not always straight forward.