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I've got Harley's T-bag. While it's designed to sit on the luggage rack, it works very nicely reversed, hooked over the sissybar but sitting on the passenger part of the seat. Makes for a nice backrest on trips and easy to take off and carry in.
I haven't taken a new pic of mine yet, but I actually have both. I really like the hard-sided bags because of the amount of carp that you can put in them. They also lock, which I like very much. Though the pic doesn't show it, I also added a detachable luggage rack that I can put a large bag on for out-of-town weekend trips with the lady, etc.
I have Willie and Max saddle bags that I leave on most of the time I keep a bottle of water and a small tool kit in them, they have come in handy when I ride with my wife and we stop and she winds up buying something she wants. When we have taken a weekend trip I use the saddle bags and a larger bag that slides over the sissy bar. Here is a pic from Vermont trip last fall with all the bags on the bike.
Like was said attach whatever bags solidly or yur paint can get scraped and marred beyond what you can buff ot.
AND if you ever have some bag come LOOSE at highway speeds it's plain freeky and dam dangerous!! It can twist ya up and throw ya to the ground or screw up things like wireing, lights, ect.