can the kindle app sync between pc and mac

Second, the Kindle PC and Metro apps don't seem to support syncing Personal Documents. Under the 'Send-to-Kindle Email Address' tab, only one device has an address, the rest just have a ' - ' and I cannot find where to add unique addresses to each device. When i go to 'Manage Devices' on the Amazon site, it lists all my devices and reading apps. First, only one of my devices/apps is letting me have an address. That app just simplifies sending a Personal Document to a email address. Is there a way to force this? I've been googling answers to this for hours with no real luck. When I get my Paperwhite I know I can load them with USB, but I don't know if my last page will then sync over to the PC and Android apps. I can open a mobi file in the Kindle for PC app but it will not populate over to the other devices. I can get them to load on my phone if I send them to my email, but they won't populate over to the PC/Metro apps. But I am having a real hard time figuring out how to do this with non-Amazon books.

I know if you purchase a book off the Amazon store, it will sync and load onto all your devices and remember your last page, etc. I also have a full Windows 8 tablet (not RT) and a Kindle Paperwhite on order, plus my Android phone.

I have the Kindle for PC app on my Windows 8 PC as well as the Kindle Metro app.

None of them were purchased on the Amazon store. The books started in epub format but I used Calibre to convert them to mobi. I currently have a lot of DRM free ebooks that I want to load onto all of my devices and use full syncing.

Can the kindle app sync between pc and mac