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Yes, though a plain SSH connection is likely to close periodically. AutoSSH is meant to prevent that.

this is easily solved by wrapping it in a "while true;". Still no download required.

Yes this works fine for most cases. Although I've had DNS-related problems I've never been able to resolve properly.

Can you expand on that? I've never seen any problems with -D

Well the DNS queries aren't routed through the proxy.

Possibly because DNS queries are trying to be UDP?

That does TCP-over-TCP, though, which provides worse performance.

I use this every day and the performance is not that bad. You wouldn't notice the difference when browsing the web.

No it doesn't. SOCKS is connection- (stream) based, not packet-based.