The OS in question is Windows 8.1

Both laptops have 100+ gig SSDs

Now suppose I really don't want to bother installing the OS again, can I just use a linux USB stick, dd the whole SSD drive to external storage and dd it back to the new SSD on the new laptop?

Will this work?

If so, what kind of issues would arise? If the second SSD is larger will I be able to extend partition or have to make a new one? etc.