New PC, Moving Software, PITA...

yep.  it's a pain.

but personally I have avoided an iLok so far - I'm not interested in what happens if I happen to lose or break it when I really need it.

so, installing, installing and installing and reauthorizing...yada, yada... for new system...that's the way it goes.

Re-regestering does not take that long as long as you are organised and keep all the data. A  ring binder with copies of the authorisation emails, Text file copies on the backup DVDs of downloaded programs etc.
 
What takes the time is the actual installation and then updating all the latest patches, that is the real PITA.
 
I would not worry too about Native Instruments or Toontrack they are pretty straightforward. (unless NI service centre goes into a self up date loop in which case try again later). NI service centre should automatically retreive all your products from your account so even if you have lost the serial numbers you should be OK.
 
Toontrack only shows 4 authorisations were pretty quick at sorting me out some extra regestrations when I was running out following some computer problems, as were Yellowtools.

I am not totally anti dongle and have a lot of experience using them in my job (non-music related), where I have five different dongles, however I seldom have more than three connected at any one time.. The plus side is easy swapping of licenses between computers and marginally easier reinstallation (I still maintain its the reinstallation and patching, not the authorizations that the real pain).
Most are Sentinel keys, they tend to be reliable and even though we have a lot of them in harsh environments I can only recall one failure, which was replaced free of charge. In the conditions they are used in if they were going to snap off easily it would have happened ny now, for sure. On the down side if I lose the little case I carry them around in its tens of thousands of dollars down the drain.
With my work software we are talking about high ticket packages and the dongle cost is a small portion of the cost of the software and always included in the purchase price. Most music software is not so high ticket. I have been put off buying some music software when I found that the cost of dongle almost doubled the price I would have to pay, making the product uncompetitive.
Worst of the worst -  with one (non music related) company you had to have a dongle, but still had to use challenge and response as well - the worst of both worlds.  Fortunately they have now dropped the requirement for a dongle.