I don't think he aimed for 4 products in a specific line, so he'd probably be miffed about how many variants there are between each.
I think the 4 iPads would be forgivable if there was consistency between the various product lines naming. iPhone _ Plus vs iPad Pro vs iPhone XS Max? That by itself is 3 different "descriptors" for their big screen devices (granted, Pro is less about big screen and more about spec stuffing, but non-tech consumers I know think iPad Pro = big screen iPad = expensive iPad).
I don't think he aimed for 4 products in a specific line, so he'd probably be miffed about how many variants there are between each.
I think the 4 iPads would be forgivable if there was consistency between the various product lines naming. iPhone _ Plus vs iPad Pro vs iPhone XS Max? That by itself is 3 different "descriptors" for their big screen devices (granted, Pro is less about big screen and more about spec stuffing, but non-tech consumers I know think iPad Pro = big screen iPad = expensive iPad).