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I've got an old 2008 Macbook which is not eligible for upgrade to anything supported at the moment. So, I am looking to buy a new MacBook Pro.
My question is,
Is it better to copy/move my HDD to the new machine and then do an upgrade or start with the clean install of OSX already on the machine and slowly reinstall all the apps I need, as needed?
Thanks.
You're five major system updates back from El Capitan, and Apple has made a lot of changes to code, file arrangements, database structures, network connectivity etc. in the meantime. Apple usually does a pretty good job of clearing away the old to make way for the new, but things do slip through. I recently killed a few prefs files from 2007 that Migration Assistant kindly transferred to my 2014 mini. Invisible files and such often gets copied too. iTunes data structures have changed significantly, with loss of artwork or metadata upon upgrade being fairly common.
Apple is pretty good, but they're not infallible. With a jump of that many years, I'd go for the clean install, followed by thoughtful installation of needed Apps, and manual transfer of docs, pics, music etc. That way you'll end up with a thoroughly modern System rather than a System that also contains a hodgepodge of used or unused pieces dating from an earlier decade.
Is it better to copy/move my HDD to the new machine and then do an upgrade
Not possible for two reasons. - The current Macbook Pros use PCIe flash storage, the drive from your 2008 model will not fit. - The operating system in your 2008 will not run on a new Macbook. So you are going to get stuck at a kernel panic page.
What you should do:
Start the old computer and connect to the local network. Do the same with the new one. When the new computer asks if you want to run migration assistant, say yes. Follow the prompts to access your old computer and then leave it alone for a while - it can take many hours to process things.
Migration Assistant will copy your user info, documents, data, and work out which applications are compatible with the new system. End result, a new computer as much like the old one as possible. You will need to update most of your old applications, 8 years is several major versions of nearly anything.
It's much faster if you put the old drive in an external case and connect it directly to the new computer. If you know how (and have the parts) do that.
