Hi Maria,
Thanks for the report. I looked into this, and the good news is that it's already been improved in more recent versions.
What you're seeing in 6.2.75 is that the asset chooser disables the Upload and Edit actions whenever an asset is selected in the chooser — this isn't actually specific to the asset being deleted; the buttons are disabled for any selected asset. To upload, you have to deselect / navigate back to the folder first.
This was improved under MGNLDAM-1531 "Asset chooser. Enable users to upload when an item is selected" (
https://magnolia-cms.atlassian.net/browse/MGNLDAM-1531), which lets you upload a new asset even while an item is selected (uploading into the same folder). It was released with Magnolia 6.3.3, so upgrading to 6.3.3 or later should resolve it.
You can see the areas involved on our public demo (login superuser / superuser):
Hope that helps — let me know if you have any questions.
Best,
Roman