In the last 7-8 years, I've tried perhaps 4 or 5 different inflatable pillows and found they usually started to leak the 3rd or 4th time used, and I never inflate them to maximum. Some have difficult to use 'pinch to use' valves, and some far easier.
What I finally settled on 3 or 4 years ago was these at Amazon
https://www.amazon.com/Lewis-N-Clar...wis+n+clark+comfort+set&qid=1582910129&sr=8-1 Not only is it a fuzzy on one side/sheetlike material on the other side covered inflatable pillow (the cover easily comes off for washing. However, after 4 washings, it's not as fuzzy as it used to be), but it also contains a 50"x38" soft blanket inside! It also comes with ear plugs and eye shield as well, that I just throw away. In the 3 years or so I've owned them (I have 3 and use them each overnight trip), I figure I've inflated them about 50 times all together. Without a doubt, these are the toughest, most durable inflatable pillows I've ever encountered. Unfortunately, one of them developed a slow leak 2 trips ago, so I'll try a bicycle inner tube patch kit and see if that works. They're also the easiest to inflate/deflate, as there's no obstruction/pinch-to-use valve. I simply pinch it to keep the air from leaking out before I can quickly push the attached plug in the hole. It looks like Amazon doesn't stock them any longer, but they're available elsewhere. Simply Google them.
Why 3 of these pillows? Due to digestive issues, have to sleep with my torso slightly elevated. So I either make up the lower bunk as a chaise-lounge with a 4" gap between, or pile up the inflatable pillows and blankets to give me the lift I need. A couple of times, I used one of the blankets in addition to the one in the roomette to stay warm as in-room heating/cooling 'control' in Superliners is slow to react and not very effective.
As for packing, I keep the blankets separately from the inflatable pillows as it gives me more flexibility to divide them between a rolling airplane-carryon size bag and a large 'gym bag' which is all I take with me, even for a 10-12 day trip as I count on using a laundromat somewhere along the way, hopefully in the hotel I'm staying at. I've also learned to find smaller sized bathroom items from deoderant to hair dryer to maximize packing space.