Don't worry about it.
The first time I downloaded pics from my camera to my laptop, it took me TWO DAYS to find them. I have since learned to pay attention to the address they are assigned and that helps. Making folders also helps --- so get that youngster to help with that.
If the pics need to be optimized to work for this site then save them to another folder. Mine tend to show up as the last additions in 'My Recent Documents'. Rather than selecting 'download' from the optimize page, I just right click then select 'save as'. When I do that I have to take the time to notice the address or create a name for it. It's easy to just click your way through it all without noticing.
Anyway, I'm on my computer for hours and hours every day and I still struggle with stuff.