To install the 5.5 upgrade you will need a working V5 installed first. So here's what I would do:
1. Install V5.0 once you get the iMac. Note that you will also need VMware Fusion or Parallels installed first, as well as a copy of Windows. Don't try to do anything until you have Windows up and working on the iMac.
2. Run the license transfer program on the old computer to get your license.
3. Install V5.0 on the iMac Windows Virtual Machine. Don't try to use it or even activate it.
4. Use the license on the V5 in the iMac. Make sure it is working before going any further.
5. Install the 5.5 upgrade on the iMac.
There are some pitfalls in the road:
- You could get stuck on step 1 if you don't have virtual machine software and/or Windows.
- Step 2 could get ugly if the transfer doesn't want to work. Make sure you have the latest patches installed before trying it.
- If you encounter any difficulty with steps 2-4 you may need Janome help.
- Once you have completed step 5 successfully make a backup of the entire virtual machine on an external drive. This is really important, especially if you use Parallels. Virtual Machine software gets updated often in search of better performance. This can sometimes cause the software "footprint" of the VM to change enough that Windows, and potentially V5.5, to think you have a new computer and demand reactivation. I also make backups of my VM software prior to updating it for the same reason. If you have everything backed up you can quickly restore it to a working state.