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Brendon, given that you already have a good camera in the Canon 550d, your a step on the way to imaging.
It depends on your ultimate objective in imaging. Some people do manage to take photos from dobs, but for long exposures on DSOs you will need an EQ Goto type mount like the HEQ5, NEQ6, etc (under various brands). You can get some decent images with just the mount tracking (assuming you align correctly) but auto guiding is the next step in longer exposures.
It's a learning curve from pure visual astronomy. There are plenty of web articles on using the DSLR for astrophtography, and some specifically about Canons. As far as the scope is concerned, you can do alot with an 8" imaging newt, and there are some real bargains available locally from Bintel and Andrews. Your major cost maybe the EQ Goto mount.
Do some research, and lots of reading.
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