Making a ladder stand off

Do the half round gutters just bend around the wood then?

1. You need to assess every possible mode of failure, ensuring the thing can cope with it with safety margin
2. There could be legal implications if you lend it to others. Don't let employees use it The uspide with things like this is they're cheap, easy, and can be made to any configuration you need any time. If you need a ladder set with odd shape for a tricky job, no problem. If you get it wrong, payback is merciless.

We may be on different geometries. Consider a bit of wood close to the width of the gutter. The ladder rests against the top edge of the gutter (or the edge of the wood depending on size). A piece of wood that's close to the width of the gutter stops the edge of the gutter being bent inwards. The wood can't fall straight down into a half round gutter. (Anyhow, use a big enough bit - e.g. a bit of 4x4 fence post - and it literally can't). It might rotate - but for the fact Bill said to wedge it.

That said, I bought a stand-off 40 years ago.