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On the subject of PIA and its equivalents, what general steps do people take to protect against a VPN connection dropping, and more specifically, what do people do when using something like a DD-WRT'd router?
boristrump-
I don't see disconnects unless it's on my phone and I'm on a train and bouncing from tower to tower and poor signal to good.
Even then it reconnects after a few seconds.
I guess this is your hardware rather than the software. VPNs are good for long duration usage, my home VPN has held a connection for weeks (since I changed my PIA password a month ago).
Velocio
It's certainly safer for you if you enter and exit PIA from different countries as doing so in the same country does make it easier for anyone monitoring both ends of the VPN to correlate which requests match up.
i.e. if you're in the UK and surface in the US... you're probably OK.
If you're in the UK and surface in the UK... think about it a bit.
If you're in the USA and surface in the USA... think about it a bit.