The Remote Watch Pass explanation was just a bit confusing when it first got announced. I was helping someone build their first one and they are now having trouble with accessing from off their network to do some automation with their Watchlist. I ended up just telling them to buy it for the month and see how it went as it seemed like it was just a paywall issue. Turns out it was something to do with their Windows setup in the end but something that just worked now being so obfuscated takes away the ease of setup and really confuses more than informs.
If you have the Plex Pass then anyone connecting to they shouldn't need the Remote Pass it so that's probably why you haven't had any complaints from people accessing yours as long as you have it. It's more for people who are sharing their library without it so if you have a few people accessing then I don't think it's unfair to ask them to chip in a bit to future proof you but I think we'll be having similar questions in 5 years time when this one expires for people who picked it up.
I'm still a really big fan of Plex but it's getting harder these days to actually recommend it while the pricing is really all over the place. My advice these days is just get it now and assume the price for things will go up and not down.