How to transfer data off HD of old iMac running OS 10.5.8 onto new iMac running yosemite

my older brother's 24" iMac running Leopard 10.5.8 is having issues and shuts itself off without notice so we got him a new 27" iMac off the apple website.
We also bought the Apple Extended warranty due to his & my computer skills are limited plus he lives in another state for a quick drop by to help with my limited skills as well.
His local non apple tech person thinks the old iMac probably has an issue with Mother board causing computer to shut itself down and suggested replacing old mac with a newer one which we did.
I was visiting my older brother who lives out of state a couple weeks ago when the new iMac arrived so I tried to transfer data off old HD to new iMac via USB cable but got error message saying the old iMac also had to be running OS Yosemite!
Due to how far back his old iMac OS version is, and not knowing where / how to get the newer OS disks needed what are his options to get data from Old iMac to new iMac?
Also, his old iMac shut down again and he has not been able to get the old mac to start back up so upgrading OS's does not seem to be an option now.
Before his mac shut down, my brother thinks someone told him that if he had iCloud set up his data could transfer via iCloud?   I have no idea if that is correct nor how to set that up.
if i remember correctly when i was there a couple weeks ago when the old iMac was running during the process of trying to transfer data I think the new computer also gave another option on how to transfer-migrate data but I don't' remember what that was?
DUE to the old imac may not start up again, can't he have the old iMac HD removed and put into an external case and plug it into new iMac as and external HD & then take files off for use on the new iMac?
any and all suggestions / help will be appreciated.
Thanks
Bob

Neil
Thanks that was very helpful for transferring files and looks like it solves the problem with not having to update the Operating Systems to Yosemite.
I forgot to ask about how does one transfer actual Programs like MS Office for example from the old drive?
Transferring files using the drag and drop process is simple enough but don't actual Programs like MS Office have a much more complicated/larger data package that may be located in various places on the old HD versus files are much smaller and are in one place?
If I remember right when i got a new iMac a few years ago, my old mac was still working so i was able to use a cable to transfer data & programs off it to newer iMac and ALL of the Programs like Office etc. transferred over including user accounts etc.? I may be wrong as its been a few years?
Again Any help & or suggestions are appreciated!
Thanks
Bob

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