Trying to upgrade computers and server on my small business office

I'm upgrading 4 computers and a server in my small business office (one for one replacement on all). Would I replace the server (computer) first and then the 4 computers or can I replace the computers and then the server? They are all Dell products.
I use a tape drive to do daily backups of my data. Can I just create a cloud backup account and put the data there and then download it back to that specific computer? I hope this makes sense. I haven't done this in years and trying to save a bunch of money
than paying some techs.
Thanks in advance, Cicely

-->The old computers and server is XP and the new ones are all on Windows 8.
Windows Server 2003?
-->I guess I better think
about this or do some extensive research.
Yeah...great.
Best,
Howtodo

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