Quality acrylic latex paint is an excellent choice for painting rough-sawn exterior plywood siding. Preservative treatment of the wood before painting is not necessary if proper construction practices are followed when installing the siding. There should be no contact of the bottom edge of the siding with soil or other surfaces where water can puddle.
As for leaving the stucco unfinished, only the manufacturer of the material can tell you what effect a winter's weathering would have on it. Loxon Exterior Acrylic Masonry Primer is the correct primer for new stucco. It cannot be used below 50° F. A-100 is a topcoat that is meant to be applied down to 35°F, yet not meant to be applied to fresh, hot, masonry surfaces.
Gloss paints are best for paintable shutters and trim because they accentuate architectural details and their finish tends to be hard and smooth.
Hardboard siding is manufactured by pressing a mixture of wood chips, binder and wax into shape and embossing with a wood grain pattern. Most of this siding is then factory-primed before shipment. To provide proper adhesion and to prevent wax staining, we recommend applying a quality alkyd-based primer before topcoating, whether the siding is preprimed or not. Once the alkyd primer has been applied, you can use either an acrylic latex or alkyd topcoat, depending on the customer's personal preference.
First, determine that the roof is indeed tin, and not galvanized steel. If it is tin, clean and rinse the surface to remove any dirt, mildew or surface contaminants. After the roof is dry, apply a slow-drying, rust-inhibitive oil-based primer followed by two coats of a quality topcoat. Industrial-grade acrylics, slower-drying alkyds and aluminum paints can all be used for the finish coats. If the roof is galvanized, make sure it is clean, dry, and sound and then apply a primer like DTM Primer/Finish, following with two coats of DTM Acrylic Finish. Use a conventional roof coating material if the roof is flat.
Vinyl siding is a very flexible material that expands and contracts horizontally with temperature changes. In fact, when it is installed, the nails are not hammered all the way into the sheathing to allow for such movement. Since dark colors absorb more heat than light colors, painting the siding brown could cause it to flex so much that it could come unfastened or, in severe cases, even cause structural damage to the house. A good rule of thumb is to avoid using a paint color any darker than the original color of the siding unless the coating is specifically designed for such use Like Sherwin-Williams VinylSafe Technology.
Both ideas are correct. Since moisture is the culprit in many cases of exterior peeling, it's important to use a good quality, acrylic caulk to fill gaps around windows and doors, joints in siding and trim boards, and anywhere moisture could get into the end-grain wood. However, you also need to make sure that moisture generated inside the house has a way to escape. The best way to "allow a house to breathe" is gable, roof, and eave vents. If you are correcting an existing moisture-related peeling problem, you may also need to install siding wedges or vents to give the moisture an easier path of escape than through the paint film. Caulking where the siding overlaps is not advisable, as it could trap moisture behind the paint, causing it to peel.
In many cases, the application of a high-solids universal primer or barrier coat will allow the application of a strong solvent-based epoxy or urethane over a previous coating. Using a barrier coat reduces the likelihood of the solvents in the topcoat lifting previous finishes and eliminates the need for costly and time-consuming removal of all existing paint.
Stay away from conventional floor coatings such as epoxies and alkyd floor enamels. While an epoxy would withstand the exposure to the pool water, both of these types of paints would be far too slippery to use around a pool. Since the concrete is new, an acrylic concrete coating like Sher-Crete Flexible Concrete Waterproofer would be your best choice.
After allowing the galvanized surface to weather for six months or chemically cleaning it to remove any oil or remnants of the galvanizing process, you can apply two coats of an acrylic latex paint directly to the metal or a special galvanized metal primer topcoated with an alkyd or latex product. Do not apply an alkyd directly to a galvanized metal surface because the oils will react with the zinc used in the galvanizing process, causing the alkyd to peel.