Dear Jenny Hersko,
Thanks for posting in Microsoft community.
I go through your description, for your first concern, the files in SharePoint library are stored in OneDrive so they follow the same restriction and limitations. Please check this article for information in detail: Restrictions and limitations in OneDrive and SharePoint.
For the second one, drag and drop/Upload button are actually the same thing and the process is same as upload the file in OneDrive, there is no specific differences between them.
Hope my reply could help you, if I misunderstand anything, feel free to point out.
Have a nice day.
Sincerely,
Sean Cai | Microsoft Community Moderator
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