Personal Item Reccomendation after Back Injury
 

I've been using my Tom Bihn Synapse 25 for years, but my deteriorating back means this is no longer a great option. I'm hoping to get some recommendations from more experienced travelers!
What I'm hoping to find in my new bag:
-Personal item size (under seat). I sit in the aisle on Alaska Airlines for the vast majority of flights--737s
-Wheeled. Prefer 2 for space, but okay with 4.
-Holds iPad, Kindle, Cables/Battery, Waterbottle, Neck Pillow (Likely Turtl) easily accessible for quick use/stowing
-Room for 15" Laptop and Meds, do not need to be accessible during flight
-Stackable on other luggage

Thanks for your help!