Thanks for the suggestions everyone. I may not have time to look at everything until after this weekend but I will go over everything to see what this issue is. A few answers to questions I saw:
I live in South Carolina, where everyone throws their trash on the side of the road.
Someone asked if they are actually popping or going flat, and they’re just going flat. There have been one or two times that an actual event caused the flat, such as a pot hole, but not this frequently. It’s been on both wheels as well.
And yes, I got a flat on the trainer.
Perhaps I didn’t mention it but the tires are almost brand new. One has maybe 30 miles on it, the other has 10ish.
I’ll have to bite the bullet and get a floor pump for sure with a gauge. I’m hoping this is the issue and my little hand pump just isn’t doing it.