I'm sure someone will provide responses to the contrary, but hasn't Apple been pretty good about providing support for quite a reasonable period of time for both their software and hardware? Apple's own recent announcement indicates that they supported various bits of "vintage" hardware (hardware support only) that was first introduced between five and seven years ago: https://support.apple.com/en-us/HT201624
The same KB article indicates that what they consider to be obsolete (not at all supported) is hardware that is about 8 years or older, with most of it being 9+ years since first introduced.
The company, Construction Materials Inc, that supplied Bob's Drywall Supply should accept a delay in payment. In order to ensure payment comes as quickly as possible, an order block (no new orders are accepted from Bob's) or a shipping block (orders are accepted but not shipped) or both are placed on Bob's account.
Now, of course, what of Construction Materials, Inc? Surely they buy the raw materials from someone and ...so on. Everyone does - or should do - the same: don't adjust the terms, simply accept that the past due items are past due and will be paid a bit later than normal.
Eventually it will hit a bank or large financial institution, and they ought to do the same: accept the situation and wait. It's costly when businesses go bankrupt and everyone knows that this situation is affecting everyone else and will blow over in about six weeks.
A NAS, something like a Synology DS218+, is fairly easy to setup. I'm not a sysadmin or anything like that, though I do have some experience with Linux (2000-2005). My main OS these days is MacOS. I wouldn't want to have my 70 year old father try to set it up, but if you're on Hacker News you probably will cope with it ok.
It's my opinion that it's more time-consuming and tricky to rip/re-encode everything. I use MakeMKV and a few extra apps to rip/convert subtitles. Handbrake is, seemingly, what everyone uses to convert to MP4/MKV or whatever... and it takes a fair bit of patience to find the sweet spot of quality, size, and compatibility.
I started ripping/converting DVDs and BluRays last year around this time and I'm still on it. Some of that is due to the fact that I've had to go back and re-rip stuff and some of that is due to the fact that the machine I'm using for conversion is about 10 years old. A BR film takes about a day to a day and a half to encode.
It's funny that you mentioned Slashdot. I was living in Portland (OR) at the time I first saw the news on Slashdot. I turned on the TV to confirm. I don't remember the rest of that day except for being jumpy, as was everyone.
I have my parents (in their early 70's) using a 2008 MBP 15". Mostly for importing and organizing photos, email, and a bit of web stuff. They upgraded it to El Capitan - the latest MacOS it would take - without any difficulties. They'll likely use it for another couple of years until I donate my 2015 13" MBP to them.
This hasn't bothered me in the least and I was fine with the change.
Before I bought an iPhone without the headphone jack I bought a SoundBlaster bluetooth adapter for my wired headphones - which I'm quite fond of - and so continued to use my wired headphones. I've only got the one set of headphones, so they stay permanently plugged into the Sound Blaster device. I'll keep it until my wired headphones die or until there are a set of bluetooth headphones with a good fit and good battery life.
The same KB article indicates that what they consider to be obsolete (not at all supported) is hardware that is about 8 years or older, with most of it being 9+ years since first introduced.