Moonshadow, you're right about the regular vinyl fading. That's why we had to paint ours in the first place. We didn't know about primers back then, so we just cleaned them up good and painted them. If/when we do it again they'll get a good quality primer coat first. We painted ours in place, just taped a bit in areas where we were afraid of getting paint on the siding. DH was afraid he'd never get them back on after prying those plastic dealies off. BTW, for anyone considering painting shutters, a little paint color tip: look at the paint strips outside when you pick the color. :) Maybe everyone but us would think of this! We wanted dark navy, so we picked what looked like a rich, dark navy on the paint chip. After the first coat of paint went on, DH came inside and said "Do NOT go out there and look at them; I think it will dry down darker." Well, of COURSE I went out and looked at them. :) They were bright cobalt blue...eek! We took the rest of the gallon of paint back to Lowes and had the guys add a ton of black to it and painted the second coat. Perfect dark navy, and a lesson learned.

My own experience is exactly the same. I painstakingly stripped, sanded and did the turp/linseed oil thing that is generally recommended to conscientious old house owners. Then I oil primed, and used SW best exterior paint. Paint has held up just fine, but I have the same need to wash the mildew away every year. I do it just before it gets too cold up here in northern NY, so it's on my list for next week. And, yup, I think the linseed oil is the culprit. I lived in this house for a decade before I did my painting project, and ever since, but never before, I have had to wash off the mildew annually. Of course, linseed oil was a traditional component of paint on our old houses (mine is 160+ yo), but the other components of the paint are very different from modern coatings. On my own house I have quite a bit of heavy aligatored, very chalky paint that is completely different from the side which I painted (which happens to be the northern exposure, but not in shade otherwise). And the rest of the paint never mildews, even in shady and protected areas. It's just the exposure where I did the painting. It's very frustrating! There has been quite a bit of discussion of this phenomenon on Old House websites, both here on GW and on others So the recommendation to use linseed oil and turps as a "feeding" undercoat has been abandonned, as far as I can tell. Though it still shows up in books on old house restoration/conservation. There is another kind of linseed oil, made by the Solvent Free Paint people. Their linseed oil is organic (whoo-eee!) and processed in a different way. I have used it (and am testing it further) in a couple of projects started this year. So far I am not seeing mildew on surfaces where I used the SF Organic product, but they have only been up for about six months, or so. The stuff is quite a bit more expensive, but has a significant advantage in being much nicer to work with. The company makes a line of solvent free paint, which I am also testing on my barns. I am not sure if you could substitute the SF linseed oil in the same recipes, but it would be interesting to find out how that works out, if you do. You can find Solvent Free Paint by googling them, but I think it's solventfreepaint.com HTH, Molly~

I think I have the same siding as you - it looks like Hardi Board. Those nail holes look wrong to me. If those are on every piece of siding then the original installer didn't know what they were doing. Except in special situations, the nails should be covered by the piece of siding above. There should not be nails down low on the siding. Since those holes should not be there, I would think that filling them would be an extra step. FWIW my neighbor has the same siding and the installer caulked the seams between the boards - the vertical seams. It looks horrible because the caulk is a different texture than the siding so it sticks out. Caulking those holes would probably give you the same result - strange shiny dots on your siding. Having said that, giving water a path into the siding is not good either. But if the house is several years old and that has not been a problem, you are probably fine. On the soffit - I would have someone finish that area with an appropriate soffit material that will accept paint well and hide the 2x4s and plywood that are there now. No amount of paint is going to make that look good.

Use a stripper(eco friendly types work ok) and remove all the old paint. Reason? If it peels now, it will peel later and take any new paint. Then clean the surfaces with soap and water and let dry completely(24-48 hours). Then use a shellac based primer(BIN for interior or BullsEye 123 for exterior, both made by Zinsser) and prime. Then use which ever paint you choose. The best paint jobs are 70% preparation, 25% paint, and 5% technique.