Bryce Kramer
From what you wrote this is not a planned ahead maneuver. Rather you are dealing with a project in full progress with lots of individual files and few folders in Project Assets and you want to order up Project Assets thumbnails into Folder 01 and Folder 02 in this example.
I see the points that you bring out in what you have been trying to do.
Let us focus on your selection (all at one time) of multiple files destined for a particular folder in Project Assets
Selecting all wanted files at one time...
a. holding down Ctrl and clicking on each of the files to go into the selection
or
b. Shift click on first file in a series, hold down the Shift and click on the last file in the series.
Then clicking (holding the click) and dragging the selection downward to one of your existing Folder 01 or 02.
Just click anywhere in the selection, holding the click as you drag the selection down to the bottom edge of Project Assets. There you hold the click at the bottom edge of Project Assets as it goes into an automatic scroll down situation.
You release the click only when the mouse cursor on the Folder 01 icon when you arrive there. You continue this routine with other files you want placed in Project Asset folders.
It works.
Please review and consider and then let me know if this works for you.
Thank you.
ATR