I had a similar problem. 
The cause was that filenames on my host OS (Windows) exceeded some maximum 
length.
All files that were shorter were correctly mounted with correct owner & 
permissions.
Howevere those that were too long showed up like this in the vagrant synced 
folder:

?????????? ? ?       ?            ?            ? test_file.txt
?????????? ? ?       ?            ?            ? test_sub_dir

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