Well, if you just want to be anonymous, no. That ip/machine is associated to your person through whatever method you used to pay Digital Ocean.

It really boils down to trust, honestly. What VPN you wind up going with greatly depends on the ethics, availability, and reliability of the provider, among other things. Sure, you can always run your own, but that is still ultimately going over someone else's network at some point during transit, plus you still have to be able to trust their ethics and consider any potential disallowed content. From a reliability/availability standpoint you'd be better off getting a VPN service, just have to do some thorough research and/or peruse the great list maintained on thatoneprivacysite.net

Edit: words.

It is probably very dependent on the reasons you are using the VPN as well as who you trust to keep whatever data you are transmitting safe.

Not all wifi points allow VPN traffic. At various coffee shops, I've had both OpenVPN and Cisco Any Connect traffic outright blocked.

Getting around such blocks (such as with a SSL tunnel) is possible, but requires more than just a default install.

Also, setting up anything other than OpenVPN is a real pain in the arse. Even OpenVPN required a fair bit of Googling to make it fully functional.

Not if you want privacy or to access content disallowed by DO (torrents).

Lots of sites (e.g. Stack Overflow) block IP ranges of cloud providers.