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Why not just use tor? If you want you can also buy a VPN with tor and use it to connect to tor later. It just sounds better than chained VPNs in every way.

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Slow, hostile exits, lots of sites block exits, can't easily pick geography of an exit. The Obscura site alo lists similar reason in the faq.

Probably because half of the websites will block you, but are fine with VPNs

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