a flag will just pull the vinyl off. You need some good wood behind the vinyl to properly mount.

If you can find a stud you can attach it to the stud. If you attach it to siding it will tear out almost immediately.

It cannot go into the vinyl alone or it’ll tear off as others have said. But it doesn’t necessarily need to go into the stud either. The wood sheathing that is under the siding should be sufficient, but to be safe you can put an anchor in first. What you’re gonna do is first predrill the holes where the mount will sit. If you are going to use an anchor, then you will need to drill a hole that’s the size of the anchor or ever so slightly smaller. Then tap your anchors in with a hammer. You can hit them directly at first but when the anchor is tapped in to the point that it is nearly flush with the vinyl, you will want to use a punch or anything small that you can use to tap the anchor into the sheathing the rest of the way so that you’re not banging/damaging the vinyl with the hammer, but be careful not to mangle the plastic anchor when tapping in with a punch. Ultimately you want the anchor to be into and flush with the wood sheathing . Once the anchors are tapped in place get the bracket and screw it into the anchors and you are done.

This will squish the siding a little under the mounted thing. You could cut open the vinyl to wrap around the thing but most don’t bother.

Yes, good thing to point out. In order to get the bracket as tight as it needs to be, the siding will be squeezed between bracket and sheathing which will cause the siding to indent in that area. This likely would remain indented even if you remove the bracket later, so do keep that in mind

Thank you for the thorough answer.

Make sure you use a trial flag for your first day or two. Here's a great one.

https://www.amazon.com/Anley-Breeze-Foot-Step-Snek/dp/B079NXS1GC

no, it need to be in wood

I assume regular stud finders won't work through siding? Or will it?

I have no clue.

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