Upgrade the 2008 to 10.11.x and then follow the steps in:
When you buy a new Mac the easiest, quickest and most reliable method to migrate from the old Mac to the new Mac is to simply connect the old Mac's Time Machine External Hard Disk to the new Mac using a USB cable before you turn on the new Mac. You will likely need a USB A to USB C adapter, you can find them on Amazon for $10 or less. When you start the new Mac for the first time it will startup Setup Assistant (SA), SA will get to a point where it asks if you are migrating from another computer, select Yes and follow the on-screen prompts and it's done! It is THAT simple.
If you have already done SA on the new computer then simply connect the Time Machine External Hard Disk using a USB cable and launch Migration Assistant (MA) which is located in Applications - Utilities - MA. Then follow the on-screen prompts.
The ONLY difference between MA and SA is MA will create a new user account that you need to log into.
Both SA and MA migrate applications (not 32 bit apps), data files & settings. They do not migrate Mac OS itself. Some professional apps such as Adobe and Microsoft apps may require re-installing their apps as they will not allow them to be migrated. As long as you kept the security keys for installing their apps, it is not an issue.
Finally, please NEVER EVER use WI-FI to migrate, this will fail in almost 100% of the situations in my experience. WI-FI was never intended to move large amounts of data at one time.
You will likely have some 32 bit apps (all third party) and these will not migrate. You can use Roaringapps.com to find your 32 bit apps and the upgrade them to 64 bit version on the 2008. Once you have done that then use Setup Assistant on the new Mac.
