I haven’t used tailscale to know how well it works but as a current zerotier user I’ve been considering moving away from it.

I actually love the idea and it’s super simple to set up but has some very annoying pitfalls for me:

1. It’s a lot of “magic”. When it fails to work the zerotier software gives you very little information on why.
2. The NAT tunneling can be iffy. I had it fail to work in some public WiFis, occasionally failed to work on mobile internet (same phone and network when it otherwise works). Restarting the app, reconnecting and so on can often help but it’s not super reliable IMO.
3. Just recently I’ve had to uninstall the app restart my Mac, reinstall the app to get it to work again - there were no changes that made it stop, it just decided it’s had enough one day to the next and as in point 1, it doesn’t tell you much over whether it’s connected or not.

Pretty much all of the issues I’ve had were with devices that have to disconnect and re-connect from the network and/or devices that move between different networks (like laptop, phone). On my router, it’s been super stable. Point is, your mileage may vary - it’s worth trying but there are definitely issues.

I have no experience with this, but happened to have seen an interview with Ludwig Minelli, the founder of Dignitas (an organisation for assisted death). The man is 90+ and still fighting for this right. I believe I saw it in a video format, but I think this was the interview - I think it’s worth a read.

I’d suggest you look up the contact for the various organisations and reach out with your situation and questions to see what they say. They’re likely to be much better sources of information.

Maybe set up a script that runs locally and pings an external service like 1.1.1.1 or 8.8.8.8 every second to see if it survives in a window when your services alert? Perhaps it’s your modem refreshing some config which causes a blip for a few seconds or something similar. If this doesn’t alert at least you can rule out that your internet fully goes out.

The other side of this would also be useful, if you could run a similar check towards different levels of your home network to see how far down it gets (e.g. ping your router, expose some simple TCP echo service on the server running all this and nc it, curl the status page of the reverse proxy (or set up a static page in it), curl the app behind the reverse proxy - just make sure to use firewall rules for this and not just put everything on the internet). Depending on where it fails should hopefully give you some idea to go on.

Maybe set up https://www.thinkbroadband.com/broadband/monitoring/quality/ to see if it registers any packet loss in those times or increased latency (although I’d still do the above as well)

I get the convenience part so the staff doesn’t have to go around do it by hand, but it just seems infeasible to do it for the other examples mentioned.

E.g. you go in, pick up item listed for $10, finish shopping in 20 mins, item now costs $15 at till… probably leave it (so now the staff has to re-shelf it) and start shopping at a place that is not trying to scam you.

For the other example, if there are a few packs of something expiring and they reduce the price for all the items on the shelf, everyone will just take the ones which have a reasonable shelf life left leaving the expiring ones.

Both of these just seem stupid.

I try to buy all ebooks, unless they only sell on Amazon.

Use the buddy system. Years ago I had a work-friend, we’d just book meetings with each other a couple of times a week, go to a meeting room and just hang out, I taught him to juggle, or we’d watch an episode from a series etc.

It was fun feeling like we got away with something, but realistically nobody questioned it because we both got our work done and it was a good company where that mattered more than time spent at a desk.