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If you use this cadd program a lot and it is worth while to you (i.e.e it makes you money) then why not upgrade to the newest version if it’s still available. If not then maybe you should find a new application that will probably be better for your work.
I know using legacy software is a comfortable and safe thing to do but if this is a money maker for you then investing in new software is probably a good investment.
If it is not making you money then the virtual machine and running your old copy of Win 98 or win XP in a virtual machine may be the best way for you, although even then it might be woth getting the new version anyway.