Sanding or paint and varnish remover are the best options. To make the wood look new is very labor intensive so few opt to go that far with the prep. I'd concentrate on the most prominent areas and forget the rest.

 

Scrape it the best you can, then spray it with PrimeRx. With a sprayer you can build up a coat 10 times thicker than regular paint. It won't sag. It doesn't work as well with a brush/roller because they pull the extra paint right off.

 

What kind of paint is on the house now? Sounds like concrete. I mean, you should be able to feather with relative ease using an orbital sander. There's some elbow grease involved to be sure. It's best to start with a carbide (very sharp) scraper. Those things, if used properly, get an awful lot of loose paint off. Once that's done, break out the orbital and sand.

You might be overthinking this. I don't really see a bunch of areas that need much feathering. Looks like typical peeling paint. Of more concern to me, are the fascia boards. Some look like they've been replaced before. Check the drip edge to make sure it is installed properly. It should have a 1/4" gap between it and the fascia so water is shed away from the wood. There's also some areas (where it's peeling the most) where wood looks to be in contact with stone/concrete. That wood will wick moisture up into it and cause premature paint failure.

 

Of more concern to me, are the fascia boards. Some look like they've been replaced before. Check the drip edge to make sure it is installed properly. It should have a 1/4" gap between it and the fascia so water is shed away from the wood. There's also some areas (where it's peeling the most) where wood looks to be in contact with stone/concrete. That wood will wick moisture up into it and cause premature paint failure.

You have a very good eye, not only were they replaced, one of them seems to have been replaced with a board filled on one end with drywall. Not kidding. It was broken and hanging out of the board above our front door. My husband and I thought it was concrete stuffed in there but no, think it was drywall putty or something like that.

And you were right about me overthinking it. I ended up throwing caution to the wind, chalk painting my frontdoor a brighter red, and painting the horrid little shed (bought the stencil on Amazon) (no idea how they got those cinder blocks shoved under there but we store only enough to make the spiders comfy in there.)

Photo of house and shed

BTW, we did paint polyurethane over the chalk painted front door and it has held up wonderfully. It's an old door that we're afraid to replace so all the imperfections were showing with the high gloss door paints I tried first. You can't mess up chalk paint, so I ignored the rules about inside outside use and did it.

 

The best way would be to float the areas a little with some exterior spackling first, then power sand that. BUT, you should spot prime any raw wood showing with an oil primer Honestly, though. I would put too much effort into it, but its your house.

 

I've used exterior spackling a few times, I'm not overly fond of it as it's generally the weak link in the paint job. If a customer wants it more than just a little near the entrance I make them sign a waiver.

 

I talking about a skim and then basically sand almost all of it off. . It will help the feathering though

 

Ya, I've had customers that wanted me to do that so none of the scraped edges will show, most change their mind when I tell them I won't stand behind it [when it's involves most of the siding]

 

Good point. I did, eventually, figure that out myself. 😏

 

You can make something look good/flat with exterior spackle, that's not the issue. The problem is the wood will absorb moisture along with expanding/contracting which will make the spackle turn loose sooner or later.