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Hey Ben, don't give up.
I also have an 8" DOB. It's a flex tube type which supposedly needs collimating just about every time they're used. The day I brought it home (I bought it second-hand) I simply took it out from the back seat of the car, put it together, extended the flex tube bits and waited for dark.
That evening I pointed it at the moon with a 25mm eyepiece and was rewarded with beautiful, crisp views. A few days later in really poor seeing and with Jupiter not very far abve the horizon I was easily able to make out the bands. This was all without any attempt at collimating.
I'm fairly convinced that in your case there's something not quite right with the telescope as others have indicated. I don't think it's anything you're doing. Tell us where you are and I'm sure there will be somebody who can help. Don't be disheartened ... you'll get there and believe me, it's well worth persevering.
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