Using Portable Home Directories with more than one client

Hi, I've got a general question about Portable Home Directories (PHD) that I'm hoping someone with more experience can help me with. I've only ever tied used PHDs to tie a Network Home to a single laptop in the past. But now I'd like to sync the home directories of a user that uses both an iMac (in the office) and a MacBook Air (on the road).
Any caveats to watch out for if we do this?
What if the user is logged into both machines at the same time?
What if the home directory on the iMac is larger than the entire SSD on the MacBook?
Appreciate any advice before heading down this path…

well... my english is not so good but i will try to explain it to you...
iTunes have a funcion that put the music in the iPod automaticaly and it will put the music of THAT computer in your iPod.
so when you conect your iPod go to options and select put the music manually or something like that (i have it in spanish XD)
or go to the "help" in iTunes > "help iTunes" then... charge iPod > charge iPod manually
this is dificult to explain in english im from argentina XD i hope you understand me XD

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