Well put. I tried a wide range of angles and it felt like from the outside, the wall was blocking the pickup point, and inside the table/chairs had collision barriers that were blocking the pickup point. Basically it felt like the item ended up in a box of collision barriers.

Fair point. :) I also checked inventory and the jacket wasn't accessible there either.

Found a few related issues:

related: https://feedback.bistudio.com/T184206

In this specific case I could aim at it (see screenshot) but not grab it, which was new to me. I've definitely see the behavior you describe where things end up on the roof, but usually I can aim at it and grab like you describe.