1. pretty sure you can configure how often you have to re authenticate. If you are not authenticated then, for example, when you try to use tailscale to ssh into a remote machine you are given a link in your terminal that you must visit (login.tailscale.com), then you perform whatever authentication like user/pass, google, or github (whatever you chose to set up), and now your terminal session is authenticated and you can proceed with accessing the remote machine. As far as I can tell using the tailscale VPN on top of your regular VPN does not work, so you must turn you VPN off before authenticating with tailscale
2. For the purpose of public internet traffic I think they do pretty much the same thing, just I control the proxy server and holesail is free. I can easily move the proxy server wherever, just using a VPS so I don't have to mess with my home firewall config.
However, I can just share with you a holesail connection string, and if you are running holesail you can peer directly with me and access whatever port I am sharing
t-y ^ peaked my interest more; gudnuf, supersu & Se7enZ
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Thanks for the feedback. I'll take a closer look at Holesail.io and try it out.
FWIW -- I also noticed on the Tailscale website that there is an integration with Mullvad:
https://tailscale.com/mullvad
Maybe that has an impact on the nuisance of turning the VPN on/off all the time, if long as one is comfortable with having Tailscale "always-on"?
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