I think there are two things here: - Do you have the budget to take a dedicated server?
- Would it work out better for you to have downtime/disruption of an upgrade/migration etc. at this stage rather than when your site is even bigger/busier?
Without any indication of what you're currently paying it's a little difficult to advise, but as Adam said you've probably got a good chunk of a dedicated server already at those limits. This is good for you at the moment since you're probably getting a lot more than you're paying for, but I can imagine that your host will look to move you onto a bigger account if they're losing money on you (which is likely).
As Corey mentioned, it's generally the system resources rather than storage space usage that are the issue. However, if you're using a lot of bandwidth then in most cases there's a reasonable amount of processing involved as well (e.g. high MySQL usage, concurrent visitors etc.) which means your host may soon start waving their T&Cs at you from this angle.
I would suggest at a minimum you consider what your next step would be if you were to upgrade to something else in the near future - what could you afford, and who would be best to buy from etc.
As for whether or not you should take a dedi or a second shared plan... if the shared plan is cheap it may work out better value, but keep in mind that you may encounter some scripting difficulties if you're trying to manipulate the filesystem on one account/server from the other.
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