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I am going to paint the exterior of my house. In the pictures below I have marked areas that I believe need to be filled. The areas marked with blue I am planning on filling with silicone, the areas in red with exterior spackle and the green highlighted area is a question of repairing or not. Am I on the right track with my plan? The area highlighted in green was hiding behind a piece of trim originally. I would like to keep the original trim removed after I paint. The piece of siding feels as though it will crack if I try to add a another nail to make it flush with the piece next to it. Is this an exclusively cosmetic issue or would it be recommended that I replace this piece of siding sticking out?

A couple other things: Do I need to cover all of the nails that hold the siding on with a dab of silicone? The house is currently brown with black trim. The new colors will be a tealish green with grey trim. I am planning on priming the entire house first then painting. It hasn't been painted in at least 20 years and the prep work I have done so far is scrape areas of the trim that were starting to flake. Do I need to go over those areas and others with a palm sander? Also, I am planning on pressure washing the house then letting it fully dry before I start painting.
 

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The top pic is too wide for caulking but most of the rest is ok to fill with caulking. The knot hole needs to either have a wood filler [bondo also works] or a wood plug inserted and caulked in place. Not sure about the bottom pic, can it be hammered flush?
 

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DO NOT USE SILICONE!!!!!!!!!

Use paintable elastomeric caulk for everything except that big knothole. I dont really know what to tell you about that. Spackle aint gonna cut it either. Maybe Durhams water putty... Its basically powdered wood filler that sets. Thats what I would use, and then smear caulk on top of that after its dry and sanded.

That first gap is a little big for caulk, but I would just caulk it a couple times.
 

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I would use shims to cover it.

Use liquid nail and pin nails then paint

Just push the shim up under the top board and let the rest of the shim cover the gaps etc.. Liquid nail the back of shim and put the pin nails to hold it until the adhesive sets.
Then paint.

Just my opinion

I would only use wood filler/putty to fill any voids
 

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The gap in the top pic and the circular hole are substantial, and caulking won't be enough. As mentioned you need to fill the gap and hole with like wood, secure it and caulk around it.
Someone mentioned Elastromeric caulk - that's a good idea.
cracks can be filled with wood filler or wood putty.
 

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Yes, the siding probably will crack from a nail. Best to drill a hole slightly smaller than the nail. Then nail it down or screw it down. Either way, hold it down in position when you do either. Don't make the nail, or screw, pull it down. I would also try to get some adhesive behind it to help take the strain off of the fastener. ...... But I can be a little anal about this stuff.

Also, you mentioned 'silicone'. Perhaps you just mean caulk, but never use REAL silicone anywhere that you intend to paint, UNLESS it says that it is 'paintable silicone'.

As for the big hole, if there is backing behind it, you could fill it with multiple layers of water putty, caulk, or even a stucco patch. Be patient though, each application is going to shrink on you, so it will take a few. OR if 'cosmetic' is good enough, smear some caulk around the hole, stick some nylon drywall tape on, then put a couple coats of caulk on top, smooth it out and paint.
 

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Discussion Starter · #11 ·
The top pic is too wide for caulking but most of the rest is ok to fill with caulking. The knot hole needs to either have a wood filler [bondo also works] or a wood plug inserted and caulked in place. Not sure about the bottom pic, can it be hammered flush?
I could make wood filler or a plug work for the knot hole. I said silicone in my first post but that was incorrect. This expanding acrylic was recommended to me for that first gap. Regarding the last picture, I don't think so. It feels brittle and I think it would break if I hammered it.
 

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Discussion Starter · #12 ·
DO NOT USE SILICONE!!!!!!!!!

Use paintable elastomeric caulk for everything except that big knothole. I dont really know what to tell you about that. Spackle aint gonna cut it either. Maybe Durhams water putty... Its basically powdered wood filler that sets. Thats what I would use, and then smear caulk on top of that after its dry and sanded.

That first gap is a little big for caulk, but I would just caulk it a couple times.
I mistakenly said silicone in my first post. This expanding acrylic was recommended to me for that gap. I don't see why wood filler wouldn't work for the knot hole. Do I need to go over all of the siding nail heads with caulking as well?
 

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Discussion Starter · #13 · (Edited)
The gap in the top pic and the circular hole are substantial, and caulking won't be enough. As mentioned you need to fill the gap and hole with like wood, secure it and caulk around it.
Someone mentioned Elastromeric caulk - that's a good idea.
cracks can be filled with wood filler or wood putty.
Would this caulking work for my application? Lightweight spackling was recommended to me for small holes in the siding. It says it is for use outdoors. Should I avoid this and go for wood putty instead? You mean for the large gap, cut a shim and secure it then seal over with caulking, correct?
 

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Discussion Starter · #14 ·
Yes, the siding probably will crack from a nail. Best to drill a hole slightly smaller than the nail. Then nail it down or screw it down. Either way, hold it down in position when you do either. Don't make the nail, or screw, pull it down. I would also try to get some adhesive behind it to help take the strain off of the fastener. ...... But I can be a little anal about this stuff.

Also, you mentioned 'silicone'. Perhaps you just mean caulk, but never use REAL silicone anywhere that you intend to paint, UNLESS it says that it is 'paintable silicone'.

As for the big hole, if there is backing behind it, you could fill it with multiple layers of water putty, caulk, or even a stucco patch. Be patient though, each application is going to shrink on you, so it will take a few. OR if 'cosmetic' is good enough, smear some caulk around the hole, stick some nylon drywall tape on, then put a couple coats of caulk on top, smooth it out and paint.
That's a good idea for the piece sticking out. I did, I mistakenly said silicone in my first post. I have posted a picture of the acrylic I bought. I will check out the water putty for the large knot hole.
 
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