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I have a 27" late 2013 iMac running OS X 10.9.5. What is the recommended upgrade path to the latest OS or to the latest recommended OS? Also, is it still recommended that one create a bootable cloned backup before attempting to upgrade? If so, how would I do that?
The model and year of your Mac will determine which macOS you can upgrade to,
read the following links.
How to upgrade to macOS Mojave - Apple Support
How to upgrade to macOS High Sierra - Apple Support
How to upgrade to OS X El Capitan - Apple Support
Before upgrading make a full back up of your Mac.
Check that third party apps you use have updates available for the new OS.
Check that your printers/ scanners etc have updated drivers and software available for the new OS.
macOS Catalina 10.15 was released recently, the latest version of macOS.
If you are considering upgrading to Catalina be warned that it does not support 32bit apps.
Your Mac is probably running 32bit apps and these will need to be updated to 64bit apps,
some updates may be free, some may be paid. Use this app to discover which apps you have
are 32bit, https://www.stclairsoft.com/Go64/. Once the list has been created you can then
contact the developers of the apps to see if they provide 64bit updates.
The model and year of your Mac will determine which macOS you can upgrade to,
read the following links.
How to upgrade to macOS Mojave - Apple Support
How to upgrade to macOS High Sierra - Apple Support
How to upgrade to OS X El Capitan - Apple Support
Before upgrading make a full back up of your Mac.
Check that third party apps you use have updates available for the new OS.
Check that your printers/ scanners etc have updated drivers and software available for the new OS.
macOS Catalina 10.15 was released recently, the latest version of macOS.
If you are considering upgrading to Catalina be warned that it does not support 32bit apps.
Your Mac is probably running 32bit apps and these will need to be updated to 64bit apps,
some updates may be free, some may be paid. Use this app to discover which apps you have
are 32bit, https://www.stclairsoft.com/Go64/. Once the list has been created you can then
contact the developers of the apps to see if they provide 64bit updates.
You should definitely have a good verified working backup at all times, but especially before any upgrades. Time Machine is probably the easiest for most users. Since you are on Mavericks and don't have access to Internet Recovery Mode yet, having a bootable backup and perhaps even a bootable macOS USB installer is a good idea especially if you don't have access to another Mac.
As far as the proper upgrade path I am not completely certain. I have seen some posts which mention some systems must first be upgraded to macOS 10.11 El Capitan before the system can be upgraded to later versions of macOS since El Capitan will install the necessary system firmware update required for later macOS installers. I don't know if the App Store is smart enough to provide the correct macOS installer or not.
Newer versions of macOS may require you to install more memory in the computer so it will run smoothly. You may be able to use just 4GB of memory with an El Capitan install, but 8GB is usually a better option especially with later versions of macOS.
Upgrade path OS X 10.9.5
