Do you have an external drive large enough to backup the contents of your OLD internal drive on the OLD iMac?
If so, here's what I'd suggest:
- Get ahold of CarbonCopyCloner. It's FREE to download, and it's FREE to use for the first 30 days.
- Use CCC to create a "cloned backup" of your OLD drive. CCC clones are mountable on the desktop, and all files are in "plain old finder format". The clone will look and operate EXACTLY as does the drive in the old iMac
- When you get the NEW iMac, BEFORE you press the power-on button, connect the cloned backup drive.
- Now press the power-on button and go through the initial setup procedure.
- At the appropriate time, the setup assistant will ask if you with to transfer accounts, apps, settings and data from another computer or drive.
- You want to "aim" it at the backup drive.
- Setup Assistant will bring over your account(s), apps, data, and settings.
BE AWARE that some older 3rd party applications probably won't run without updating. You'll just have to check each one to see what works and what doesn't.
BE AWARE that iTunes will probably need to do some kind of an "update" on your old library.
BE AWARE that if you used iPhoto before, that library will automatically open in Photos.
HOWEVER, if you wish to keep using iPhoto, you can do it by locating iPhoto 9.6.1 and installing and using that instead.
I don't use any iOS devices, and I have never used iCloud, so I can't say how synching will go with those areas.
But I think you'll find that "migration" will go quite smoothly by doing so from a cloned backup drive.