Sleeping pad idea: thin pad, plus two inflatable pillows

Side sleeper here. I wish o had done this long ago but for several years now I use a ZLite and a Nemo Flyer. I also place folded clothing and smooth stuff under my shoulder to head region to elevate that pet slightly. And my puffy as pillow.

It might work but a thinlight has very little insulation so be aware of that.
Normal pillows have a lot more give than inflatable ones, especially on a mattress compared to the ground, you’ll have to experiment with the amount of air.

Inflatable pads with long baffles tend to be most comfortable for side sleepers, this one from Big Agnes, for example, but you’d still want a pillow pad and it may be heavier than you want.

https://ultralightoutdoorgear.co.uk/divide-sleeping-mat---regular/

A closed cell pad under an inflatable pad is pretty comfortable. In the winter, use them the opposite way, and it has the added benefit of being pretty warm.

I'd die if I try to use a Thinlight to sleep!! And two inflatable pillows are really not that stable. I tried, and they go all over the place. I am now usign a large Zenbivy inflatable (with a Flex mattress), and I stuff the pillow case with some cloth. It seems to work. The large zenbivy pillow is a generous 4" high.

I am in the same boat. The comfiest air mattress I have tried is the REI Helix; it's a little on the heavy side and my arm still fell asleep this past weekend. I think hands down the most important part is the pillow height. I'd say at minimum you need 5" height and even the largest inflatable pillows are usually 4". My current system is a foam pad (or two) from GGG, Trekology 2.0 inflatable pillow, alpha fleece on top and to top it off, I use a buff to keep it all together. That being said, I ordered the new Zenbivy pillow to test out since I think the key is to have a tall enough inflatable with something soft stacked on top. I'll experiment with the foam pads. They weigh about 1oz each but honestly, I don't give a shit about UL if it means I get more than 5 hours of sleep.