Hey Rick,

I do cover several questions specific to wearing a bag sideways in THIS article. 

But to answer your question:

What about emptying your bag?

Emptying your bag will require some practice, but I find it easy and just as convenient as keeping my bag vertical; I also notice very little difference when emptying a bag full of loose output vs thicker. Removing your bag from a typical support band is actually quite quick and easy to do, and you don’t have to fumble around or anything.

Depending on how you empty your bag, you may find it more or less difficult when your pouch is sideways. Because I tend to kneel when I empty my bag, I find emptying this way to be easier.

For those who also like to rinse their bag out after emptying it, I can confidently say that you won’t have any trouble doing this.

With that said, if you wear a 2pc appliance with a mechanical coupling then you can also have the best of both worlds by rotating your appliance when emptying it or when you don't want it sideways. Instructions and FAQs about that can be found HERE.

Let me know if you need help with anything else.