I've been in plant engineering over 25 years.
Q1: Yes, we buy obsolete controls hardware on eBay, Radwell, and other industrial surplus sites several times per month.
Q2: We have multiple production lines relying on obsolete PLCs, drives, etc. that if it failed could not be swapped out for a new generation component without a significant project and extended downtime that would not be tolerated by management. Even when multiple upgrade EWRs have been submitted in the past, managers usually act surprised like they had no idea the line was at risk of going down. I tend to forward old emails they were copied on and cancelled EWRs where they were listed as approvers to remind them of proposed plans to mitigate risk that weren't funded. They don't like it, but I don't care.
Q3: We have boxes of failed / known to have issues controls hardware that are obsolete and hard to find, but we can't send them in for repair due to cost-cutting. A couple times we've had a drive failure on a machine and sent that drive in for repair and were told the repair shop can no longer source parts to fix it. Then we send one or more failed devices from our junk pile (same model / part number) to the shop and they were able to combine parts from 2 or 3 bad drives to make one that works.
I also keep a list of obsolete part numbers for hardware that we don't have spares for and are likely to cause significant business interruption if there is a failure. I try to copy and paste them into the search bar once a month or so to see if I get any hits on eBay, Radwell, etc. When I do find an item, I have to do a deep dive into past work orders to come up with an estimate of when our next failure will occur, how long the line could be down, and what alternatives have been considered in order to justify buying used/surplus spare parts that are often priced < $1,000.
I once had a plant manager ask me why we shouldn't just run to failure and then order the used replacement part from an industrial surplus company. I explained that I'd been looking for this item for over 2 years (since the last failure) and this was the first time I had found one. He responded that they must not sell many and would probably still have this one when and if we ever needed it. Better for them to hold the inventory on their books instead of 3M's books in his mind. Even if they didn't still have it when we needed it, he was confident we could "leverage 3Ms size and influence" to have a repair expedited and returned within 24 hours. The used part was priced at less than 25% of what the repair and air freight would cost and the production line was running 24/7 on a 4-crew rotation. You can't fix stupid.