I would wait for the rumored OLED iPad refresh early next summer and upgrade to that.
I would not wait—if you need to upgrade now then do it and take advantage of Black Friday discounts. What the next iPad brings (OLED, Face ID, thinner bezels, wireless charging, etc) is based on speculation and someone’s wish list.
You’ll really see the benefits of an iPad Pro—and appreciate the 120 MHz Pro-Motion display and fast processor—if you’ll be using certain apps that require precision input with a stylus, like the superb Apple Pencil. Apps for handwriting, taking notes, annotating PDFs, technical drawing and illustrating, sketching and coloring, photo editing, signing documents.
And if you enjoy viewing photos and watching videos on the iPad, you’ll benefit from the larger screen of the iPad Pro 10.5, which is noticeably larger than the Air2.
But, if your use case is mostly web shopping, reading, emailing, and playing games (non graphic-intensive games), then the iPad Pro will not be a substantial upgrade.
I’ve a friend who has a basic use of the iPad. She fell in love with the Apple Pencil and she loves to color. She upgraded to the 10.5 after I suggested adult coloring book apps. She’s happy—it’s therapy for her.
