You DO NOT WANT to "clone" your old hard drive (from a MacBook that's several years old) to a new MBPro.
Some software (particulary the system software) on the old drive may be outdated and shouldn't go on the new one.
If you can get the two Macs connected to each other, you can use Migration Assistant to move some things over, however, I wouldn't recommend even migrating your old account(s). Instead, create NEW accounts on the NEW MBPro, and "manually move" things over.
You can't manually copy the "home" folder in its entirety.
However, you CAN copy the CONTENTS of the folders in the home folder from their respective locations on the old Mac to their respective locations on the new one.
As for applications, you might do best to "reinstall where possible", ensuring that clean copies go onto the new drive.
I can't help with Windows as I've never used it on a computer that I own.