Automatic Category/File Import from Folder/File

Hi.

1) I am thinking to buy a subscription for Dropfiles.
But there is one functionality, which i want to be sure, that it is possible.

Please imagine I have a Folder on my windows dekstop with lots of other folders inside.
In each of the folders there are for example 10 documents and maybe also other folders.

How can I import the documents assigned to the correct Category (my folder structur)?
In PhocaDownloader I was able to to upload my entire folder via FTP. And Phoca created from all Folders (Inside the Folder) a Category and assigned the right documents to it.

Is there any possible solution in Dropfiles to upload and assign documents this way?
Because I dont want to create 200 categorys for example. So actually you can call it Batch Import or something like this...
Is it possible?

2) Does the Google Drive plugin recognize folders in Google Drive folder, so it creates categorys from folders? A friend said, there is an issue that Dropfiles create empty files with the title of the folder if you have a folder inside a folder on GDRIVE.

Thanks!