I will be of little (if any help) but thought I would share what I know. AND I realize I know very little. First I am in a similar position to you(waiting on a new lap top). I did order ?Laplink PC mover?.
Information that may help a little regarding ?transferring software?. I have spent many hours searching the internet for ?reviews? of different options for ?migration?. Started with searches for Laplink. Only one positive and it was written as though someone was copying the ?box?.
Finally switched to ?search? using DNA migration. Learned more. Basically there are two different ways ?transfer software? work. All have faults. Not going to go into the details but PC Magazine did an article a few years ago?comparing different software.
With my computer I did order an XP manual (400pages). ?hopefully some help there.

One magazine writer did imply there are ?not so legal? ways of transferring ?protected? data?.I would like to know more about that as well as the answers to the questions You asked.

Bottom line. I hope You get informative responses to Your post. So I can learn.
Right now I am going to return my Laplink as it has been received and is a 2004 edition. Not going to open the box to see how well it works?.too many negative users?.of course there must be thousands of happy users who are not writing positive reviews.