The more I travel with the convertible backpack, the more I am finding it possibly not as convenient as the bulky roller.

I am 5'8" 155lbs, and my convertible is always between 15 and 20 lbs. The bulky things I carry are a 4 lb laptop and at least 1 packed pair of shoes. Next time I will try using my old roller to see if this feels more convenient.

I'm not sure what options you have other than trying to split up your bag into 2 things. Perhaps a large backpack and a carry-on tote?