The upload is still an issue, for whatever reason. I also had issues with iPad images, and I also revert to my laptop for iModeler uploads. The laptop is old - a new hard drive installed last year, but the issue noted is more recent so I can't put it down to the hard drive.
Another query for future reference - the Headlines uploads are plain formatting, no bold/italics etc., but when a comment is posted within an article and one wishes to edit the comment afterwards, the full provision of formatting is available (at least I believe that to be so in Headlines responses). There are apparently restrictions in place in some areas and not others, presumably to do with the platform in use. I note the Headlines exclusion simply because if I prepared an article off-site in Word or similar, to copy and paste into the Headlines article, none of the Word formatting is retained, apart from the basics, e.g., book titles italicised in document form lose their italics when pasted into a Headlines.
Anyway, I'm not a 'code monkey' so my practical knowledge of such things is limited, but with any future upgrades it might be worth noting, to improve the site experience.