Just some random thoughts here:
1-after fighting with every manner of authorization there is, the ONLY system I like better than iLok is the Waves on-a-USB stick. Opinions vary
2-You're dealing with computer/software that is more than 10 years old
That stuff doesn't last forever(and you would be mistaken to expect it to).
3-if its important(and I assume it is), then cover your ASSets. Buy the iLok insurance(ZDT) and have a spare iLok 2 or 3 on hand(consider that all of these expenses pale in comparison to the cost of outfitting even a basic analog studio).
4-re changing workflow; I get it. Old habits dies hard. Moving to a new DAW would be a serious PITA, for sure. But moving to the current version of PT is fairly painless and your old projects(assuming they are not in SD II file format) will open, minus some plugins.
5-A move into the present will yield tons of new features that you will love!!!
And you won't believe how powerful current computers are(I recently bought a used HP Z820 12 core, 3.5GHz, 64GB of RAM and SSD loaded with Win 10 Pro for $1200
6-last 2 cents on iLok, I've been using them since PT7, have owned maybe 10 of them and never had one fail, ever(but I STILL pay the annual ZDT coverage) I just spent 2 days cursing and wrestling with IK's authorizations and hated every minute of it(enough that I may drop all their stuff and move on without them)
