For me, it really helps to go to the store and try out each size. I usually bring another bag filled with stuff, so I can test out how the bag feels under load. When I buy a bag, the smaller bag goes into the larger bag. Simple enough, right? One more thing: when choosing items to bring, at least try to emulate a typical day's worth of contents, both in volume and weight, and pack them into the tester bag just as you would any other load.
So now you're at the store, testing out bags under load. What do you look for?
First and foremost, I look for comfort. How does the strap sit on my shoulder? Where on my back does the bag naturally fall? Often, on smaller bags, the strap is built tighter on the shoulder, and the bag sits quite highly on the back. On the other hand, larger bags tend to have longer straps, so you can get a somewhat wider strap contact area and a lower back position. Wider straps also distribute loads over a larger area, but can be irritating to people of narrower build.
I also look for the placement of accessories. Chrome bags, for example, have a removable velcro strap that you can attach phone holsters and such to, and is located on the strap pad itself. On the other hand, Timbuk2 bags generally require you to attach accessories to the strap itself. Only one of their strap pads can take accessories directly.
There are advantages and disadvantages to both of these systems. With the Chrome system (which Seagull and Mission Workshop and probably ReLoad also use), the accessory is held tightly in place, so it's always there when you need it. On the Timbuk2 system, it can slide around fairly freely, so I often find my phone holster has switched position after some hard riding.
On the other hand, this also means that your accessories are generally accessible, an advantage that Timbuk2 has over Chrome. With the smaller Chrome bags, the strap pad is shorter, and if you are a bigger person, you will find your phone holster hovering over your shoulder, where it is practically useless. It is for this reason that the Deluxe Strap Pad that Timbuk2 sells isn't really worth buying.
Chrome Metropolis and Timbuk2 D-Lux Messenger. Note the Velcro strap on the Chrome vs the rigid webbing on the Timbuk2 for carrying accessories. The pad on the Chrome is a little bit wider, as well. Finally, the length of Chrome strap pads scales with the size of the bag. Timbuk2 pads only come in two sizes and two widths.
The next thing I look for is scalability. It is pretty intuitive to build a bag to comfortably carry large amounts of gear. All you have to do is expand it outward. However, it is far trickier, and requires more extensive thought, to build a bag that carries small amounts of things comfortably at the same time. Often, extremely cavernous bags "deflate" and sag uncomfortably with only small loads. After testing the bag under load, remove about 75% of the stuff and see how the bag fits.
Finally, I ask myself how big (or small) a bag I actually need. There is a kind of confirmation bias inherent to bag sizing, and it can become quite an impediment to comfort. For example, a large bag that scales well is a great idea on paper, but there's a chance that you'll find yourself over-filling it if only because you can.
If you find your daily carry to be too small for the bag, then you may want to size down instead. In the same way, if you have trouble fitting your daily carry into a bag, then getting a larger size may be in order. Over-filled bags are uncomfortable, and you'll have some space for contingencies!
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