So this part is only for the true paranoids
Without TLS interception then the ISP doesn't know anything about the transfer except for volume of data. They might be able to guess "this is mostly upload" based on volume, but that's about it. They can't easily guess how many files (if you're doing large files) because of multipart interleaved uploads.
Now someone with a MITM proxy that can see the data can not see the raw filename nor the raw file contents in a properly configured crypt
wrapper. But there is still side channel leakage; they'd see the http headers and so would know how many files, the size of each file, the directory tree structure (even if not the directory names). They might be able to make inferences ("Hmm, he's always uploading 4-9Gb files; these are probably DVD ISO rips").
We lose a level of protection.
Is it something you need to be worried about in America? Probably not. PRISM likely wouldn't flag anything because of this.
If you're in China it might be enough to warrant state scrutinity.
Kazakhstan which is forcing government CAs on all devices? I dunno...
As I said...it depends on your level of paranoia