I'm sure you will find differing opinions, but the cloud iLok thing(to me) is only something I would use in an emergency or while traveling. It requires a 100% solid internet connection or you can get shut by the slightest hiccup in connection. If you need that for travel, its easy enough to move licences back to the cloud if that's your only option, but using a physical iLok is safest(but do get the "iLok Buddy" or any short USB extension so you don't risk bending or breaking the iLok
(and DO buy the ZDT insurance AND keep your iLok refreshed for that replacement coverage, even if its only for 1 of your iLoks)
