I don't know, I've not updated more than 2 versions at the time.
But in any case, always backup before you upgrade, then there is no issue, I wouldn't even do 10.58 to 10.6 without a backup. In fact you should backup on a regular basis, Apple hardware isn't designed to last much more than the warranty period, you have to expect a serious system failure sooner or later.
Also, it's generally better to do a fresh install, than it is to upgrade an OS.
If it was me, I'd backup my existing machine (using time machine).
Wipe the machine
Install 10.8
Restore what you need from time machine.
I don't know, I've not updated more than 2 versions at the time.
But in any case, always backup before you upgrade, then there is no issue, I wouldn't even do 10.58 to 10.6 without a backup. In fact you should backup on a regular basis, Apple hardware isn't designed to last much more than the warranty period, you have to expect a serious system failure sooner or later.
Also, it's generally better to do a fresh install, than it is to upgrade an OS.
If it was me, I'd backup my existing machine (using time machine).
Wipe the machine
Install 10.8
Restore what you need from time machine.