Oh interesting. Maybe it's an issue with my USB then.
I'll try with a different USB and create the image using the libre USB creator instead of Ubuntu startup disk creator.
Update (a bit of a long one):
Tried a older usb using libre usb creator. Loaded only my test video, and it worked!
Loaded a bunch of other videos, then the problem came back.
Removed all the videos I just added, working again. (side note, that made me think i could go back to my other usb by removing all videos but my test one, this did not work)
Started loading in videos one by one (thinking a specific file was the problem), and it seems like this workflow kept LE working the whole time!
side note on how I'm loading videos - pluggin in the usb to my laptop and copying files into the STORAGE->videos area
Since this little project is only for my son to watch his small library of videos, this will work for me
I am curious though why my copying over a bunch of videos would make it falter in playing while copying over one file to then launch LE to test it would have it work.