In regards to the iTunes Store support failure, I've decided to continue purchasing à la cart TV content via iTunes due to how much better it works with my setup - namely because I can't download episodes from Amazon to my Mac mini and must stream them with occasional picture quality issues.
For HBO and Showtime I'll most likely resubscribe via Amazon. Showtime will cost less than via iTunes, and can be added to Prime directly. HBO NOW will cost the same, but must be subscribed to via a device - so I'll probably get a Fire TV (as opposed to one of Amazon's tablets) as it supports 4K (unlike the Apple TV). While I don't have a 4K set yet, I do plan to get one. I'm holding off on resubscribing to them for a bit; for Showtime I'm waiting for Shameless to start back up, while for HBO I'm waiting on the new Westworld series to start. If I've not yet purchased a new TV I'll just set up the Fire TV on one of my 4K monitors.
Last year I'd started to re-rip my CDs as I'd originally ripped them using 128 kbps AAC (MP4). When I did that I decided I had more than enough disk space and have been ripping them using Apple Lossless. Due to this I've been buying CDs again, and most likely won't buy music from iTunes anymore.
So I went to repurchase Killjoys Season 2 this morning and surprise, surprise, it's back to $19.99
Addendum: in regards to Lossless - I only use it on the Mac, not my iDevices. There's an option in iTunes to have your Mac do an on-the-fly conversion to 128/192/256 kbps AAC during the sync process. You have to scroll to the bottom of the Summary page to find to it, so it's easily overlooked:
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