My opinion is that you should travel with items that you can still be able to maneuver/carry on your own.
In this case, sliding backpack onto a wheeled case would help but if for any reason it tips over, or things don't work as properly, you should still be able to carry the backpack on your back.
Maybe this is from my days traveling alone with a baby. I used to count on the stroller to help carry things, but one time the door to the area in aircraft where they put "gate checked" items didn't open. This was after a 9 hour flight abroad so I had to carry lots of baby supplies, clothes, etc. Everyone had to retrieve those bags/items in the carrousel with other larger suitcases.
I had a 6 month old baby, a carseat/bassinet (that clipped on stroller but no stroller), my small purse/fanny pack, a backpack and a small/light duffle bag. I put baby on wrap and carried her on my chest, backpack on back, duffle bag on one hand and carseat on the other. This was during an international connection. I asked for a wheelchair to help me carry bassinet/items and they couldn't give me one because it was for people only (mind you this was in a South American country). And no "cart" available either. I was able to carry it all on my own but walked slowly. Luckily, someone saw my struggle and helped me carry the carseat until immigration. Once I retrieved stroller and put baby and all other bags on it, I then pushed stroller with one hand and the suitcase with the other to luggage drop-off and connecting flight. Since then, I only traveled with things that I could handle alone not counting on helpers like a stroller (or wheeled bag to help carry heavy backpack).
One good thing about traveling with a carry-on backpack is that it is unlikely for it to be gate-checked. Airlines usually prioritize roller bags to be gate checked if overhead bins are full instead of a backpack.