As for the badgering about browsing history, this doesn't seem like a Chrome feature I've ever seen or heard of, and is likely caused by an add-on you have. Browsers don't care about how much cache, history, or bookmarks you have. It's all data in a sqlite DB file on your hard drive.
With regards to the NTFS partition, it's possible the partition table is corrupted, but flash memory doesn't last for ever either so it could be a hardware issue. My first suggestion would be to see if a Windows machine can repair the drive. Start > Disk Management. See if the drive or a partition on that drive is showing. If no, right-click, go to Properties, Tools, Error Checking, and click Check. If the drive isn't detected at all, try moving it to a Linux system, which dmesg would give a better idea of any issues with it. If you can see the drive there and can mount it, you can recover the data and try re-formatting the drive and putting the files back.
Beyond that, I don't know if any tools you could use to recover data from the drive. If you find any good ones, please let us know so we can bookmark it for future reference.
Jeremiah Bess