I've had no problems at all
I did a fair amount of reading before selecting this rack. The comments on every rack I considered included many complaints about rust appearing quicker than buyers expected, so I just took that as a given. I bought mine June of 2012 and 3 years later I have no rust at all. (knock on wood)
The bag and rain cover seem to be great quality but I have not yet been caught in the rain while using them so I can't speak to the ability to keep stuff dry.
I, too, have found attaching the bag to the rack with the straps to be somewhat difficult. If there is a "right" way to do it, it isn't obvious to me and every time I just end up messing around with it until I get it secure.
One other issue is the bag is so roomy, it's easy to overload it and exceed the weight capacity of the rack and trunk lid. So be careful when loading up the bag.
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