The following is intended to be a detailed guide to answer the question, "How do I choose the best VPN (for me)?" The reason this is a hard thing to help people with, is that their needs and level of technical knowledge vary greatly - there is no one perfect VPN, they all have at least some flaws and some will just flat out be better for different people.
I very well might have forgotten to add a section I intended to, said something that needs clarification, or was just sleepy when I wrote parts of this guide, so I intend to update and expand it as needed.
I'm assuming that if you're reading this far, you have at least SOME knowledge as to the basics of what a VPN is, so I won't cover that here. This will be heavily emphasizing the need of a VPN for privacy, but I will echo and expand on other use cases as well towards the end.
A WORD ABOUT TRUST
No matter what reason you want a VPN, you want to know that the service you choose is trustworthy and is not compromising your data. Even if you're only concerned with geo-unblocking or other non-privacy uses, keep reading. I'll get more into this in the "Privacy" section, but it's important for everyone to be exposed to it at least a little.
A preface regarding privacy and trust, from another thread I made a while back. This applies to every company, but I would suggest especially so for VPNs.
We live in a society where privacy is undervalued and under assault daily. Some people eventually notice this and discover that they do value their own. They set out on a pilgrimage of sorts to educate themselves and learn about tools to help them protect it (as I did when I started my project). Because we depend on each other for direction and others to write software and run services to help keep us secure - TRUST AND TRANSPARENCY - are paramount.
However, transparency comes before trust.
A WORD ABOUT VPN AFFILIATES
You may have started your search for a VPN by looking for "VPN Reviews" in your search engine of choice. if you had, you would have gotten page upon page of what seem to be harmless review sites, top 10 or blog style reviews of different VPN services. You may even be coming here for confirmation of what you were told on those sites. The sites making these recommendations are, in almost every case, paid by the services they review and recommend. They are beginning their business relationship with you, with what essentially amounts to a lie. The technical term for this kind of marketing is "native advertising" and it's abuse is a huge problem in the VPN industry.
I purposefully made a point to capture this kind of data on my VPN Comparison Chart. There you can find information on services that have affiliate programs, the specific policies they have for them and whether or not the affiliates act ethically, essentially what the services tolerate from those representing them, when it comes to persuading YOU to buy into the information they put out.
Note that not all affiliates have to be bad actors and simply having an affiliate program is not necessarily grounds for mistrust of a VPN, but rather when those services allow their resellers to generate referrals by hook or by crook. If you see a service appear over and over again on the kinds of sites mentioned above, there is a good chance they are making money from, and are perfectly okay with these kinds of deceptive practices as a part of their business model. They often will claim that it's just the affiliate doing this, and that they can't control what others do. This is false. Affiliates, like anyone entering into a business relationship with someone, agree to certain terms put forth by the service hiring them. If a company doesn't expect and enforce certain standards from their affiliates (not spamming, not breaking copyright, disclosing who they are, etc), they are approving these methods, and are not worthy of your trust. If they are willing to lie to you before you even buy into their service, the stage is set for them to be dishonest with you when you interact with them on a normal basis as a customer.
IF YOU'RE CONCERNED WITH PRIVACY
As a lawyer represents your legal interests, a VPN service (among others) represents your privacy interests. If a lawyer does something to violate your trust or is not honest about some aspect of their representation that could affect you, you would discard them and you'd be right to do so. Likewise with a VPN service. There are many out there that are not worth your time or money. Unlike a lawyer, a VPN can be put together and promoted by anyone with access to a computer, the key difference being that you would never even see their face.
If you are looking for a VPN for privacy purposes, you already believe you cannot trust certain parties. Those parties might be companies whose websites you visit or maybe even an oppressive government whose mass surveillance is encroaching on your rights. You are being put in a position where you must rely on someone other than yourself for protection and the last thing you need is one more party that you can't trust.
This decision is an important one, and not just any VPN service is worthy of that trust. You're trusting them to know what they're doing - to be able to operate a competent service that will protect your privacy. You are trusting them to be responsive to new technical and geopolitical threats to their operation. You're trusting them to be honest with you in the way they do business so that when you are shopping and comparing, you are getting accurate information.
... to be continued. Read the part 2 here: How To Choose The Best VPN - Fourteen eyes countries, No Logging, Anonymous Payments.