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Not dumb at all. I'm doing this on a $5 droplet and it's faster than any of the commercial VPN's I'm currently paying for. It's a little less privacy protective than many VPN providers however - Digital Ocean will for example forward DMCA violation nastygrams they receive from content owners.

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You'll get recapcha'd like crazy.

Also some e-commerce sites will refuse purchases when made from hosting-allocated IP ranges since it's commonplace for fraud.

At least for me on linode, it's less-bad than others I've seen. Google doesn't typically get nasty; I think I can only think of a few sites that are especially bad (linkedin and arstechnica forums are two that come to mind). That probably has to do with me using the same IP for ~2yrs now, so it doesn't have reputation problems.

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