Well, that’s not to hard.

  • Easiest is a wired LAN/Ethernet possibility without captive portal. That’s easiest because it would be plug and play!
  • Next up would be wireless without captive portal. With GL-inet’s gui is will be relatively simple to connect to wireless networks.
  • Harder is when captive portals are at play. So next would be wired LAN/Ethernet possibility with captive portal. This can be as simple as plugging in an ethernet cable; connecting one of your devices to the travel router and having a awesome “Login to use this wireless network”-notification popping up, which instantly takes you to the page in which you accept term/fill in any credentials/ticket you need to fill in. If you’re less fortunate you end up having to very much troubleshoot everything to figure out what tricks are being done to prevent you from using a travel router to use a captive portal.
  • Hardest would be wireless network with captive portal. This has all the fun of wired LAN/Ethernet possibility with captive, but with extra fun of possibly having fairly shitty wifi connectivity.

So basically: “Does accessing the internet require using a captive portal?” is in most important thing. But that’s already a pretty technical question. So as a more generic rule: Pretty much any accommodation selling wifi-cards/tickets for a certain duration/amount of data usage uses captive portals.

Additional points I always try to obtain while travelling is having a VPN service working as well in case I do not happen to trust the network or because firewalls block things I rather do anyway. In some places that can cause additional troubleshoot in case the accommodation has a firewall in place.

How would you see that troubleshooting work?
I mean you “might” not have internet yet or would you have 4G/5G on mobile?
What time zones are you travelling most in?
How frequently do you change accommodation? Most work is generally getting it working first time. Generally when set up at an accommodation, it will keep working; Might need a restart every once in a while, but that’s generally all)