I would go with latex. I don't use much Pittsburgh, but I am sure they have a premium acrylic paint. You just need to be sure you buy their top line paint. I would use BIN on the sills or an acrylic bonding type primer. BIN would be safest because it sticks the best and will kill stains, but it stinks. A conditioner is a good idea if you are worried about the paint drying too fast. It depends on how fast you can move and how good of a painter you are. Dynaflex 230 is a fine choice for caulk. You do not want to use that for filling holes though. Caulk is only for filling gaps between two pieces of wood. For the holes, you can use any shrink free type of spackling, preferable something lightweight so that it sands easily, but definately do not use Red Devil and any type of product that says it is has a vinyl component. I just use the tinted drywall mud for filling holes. I leave a very small mound of it on top of the hole to account for the shrinking and then when dry, sand it flush. And, when I say small, I mean really small....so many DIY'ers when using this technique lay so much spackling on top of each nail hole that they end up having to sand forever. I don't think it is realistic to to just pick up a sprayer, practice on a few doors and then spray your trim with good results. The trick to really great spraywork is that you want to put the paint on heavy, but not so heavy that it runs and sags. Finding that zone can take years of practice. Some people can pick up a sprayer and learn it pretty quick though, but I just think this is a very small percentage of people. If you have natural great hand-eye coordination, then maybe you can do it. It's very hard to fix paint runs.

>>I know this post has been ripening a while, but I just saw it - all quality house painters recommend brushing on paint - forces it into the crevices and protects better. Hope this reached you in time This is generally true for wood because wood is very porous. You want deeper penetration of the paint into the wood for greater protection. The fiber cement siding is a different animal entirely though because it is not as porous, so I think spraying would be fine. You always want to read the instructions that came with your siding for application instructions or if it is a James Hardie product you can visit their website for paint application instructions. >>I'm in the same boat. Just finished putting on about 250 pieces of Hardiplank on a new home we are building. Originally I planned on renting a sprayer and trying my hand at spraying as much as I could. The more I research, the less this looks likely. Still wondering if it is a possibility, or a definite NO. (?) Would the paint have to be thinned to the point you are compromising it? Planning on using SW Duration paint. Further, my carpenter-in-crime says he thinks I should caulk each plank on the bottom, or its not going to look right once its painted. Oh lord.Does your carpenter friend know anything about building and construction? Moisture needs to get out from behind the siding and it escapes through the gaps under each lap of siding. This is also the reason that you see tiny weep holes on the bottom of every piece of aluminum or vinyl siding. Caulking under each piece of siding will result in massive paint failure. When painting any type of siding, I always try to even minimize the amount of paint I put under each board so that I do not plug up those gaps with paint. I have never sprayed Duration, but if you have a good airless you should not really have to thin any paints if you run them through a good sprayer. Read the can of Duration for recommendations in regards to spraying.

Update - I just finished the 2 rockers & a small round side table...pheww...that was a lot of work! I started early this morning first washing the pieces, drying, scrubbing off loose paint w/ a wire brush, wiping down, sanding, wiping down w/ damp cloth. Then first coat, let dry for 1 hr. Second coat, let dry, then checked for touch-ups. They look great! Don't know how long the finish will last, but they look as good as new right now. I used Rustoleum paint for outdoor furniture in white/satin finish. I am lucky that it is a cool, clear, dry, not-too-windy day here in NH. I was able to set up and work outside and everything is getting a final dry on blocks of wood in the back yard. The prep work, sanding particularly, took longest and was a pain - so many slats/support dowels & joints to get around. Would I do it again? Yes. But not tomorrow, LOL!

Leave them if they are in decent shape. They are a classic style. I have very similar black stools with white ice granite, & white shaker cabs. And three kids ages 11, 9 and 5. Your kids are even younger, so the chairs are still going to withstand a few years of abuse and I think painting them will only leave them more susceptible to chipping and scuffs because you'll be refinishing over a factory finish. I say leave them, let them get good and dinged up in the next few years (mine are from Target and are surprisingly forgiving to scratches and chips). Then replace them all together - maybe with an updated style - when you decide to do a kitchen refresh in a few years.