From that and similar experiences, here are Gordon's Rules of Engagement for software and services.
- Is there obnoxious DRM? (Some DRM is understandable, but it shouldn't be obnoxious.)
- If distributed on CD, can the product be used without the CD running?
- Look at the installer. Drag and Drop is fine, but if it needs an installer it better be Apple's installer.
- Inspect the uninstaller. The best apps don't need one - just delete the app. After that look for something built into the app. Then look for something that downloads with the app. If there's no installer stop immediately.
- If it's software, is there an full feature trial period? Limited feature trials are worthless. I need at least a month, or, better, 10 days of use (which may take me months).
- Who makes the product? What's their support site like? Can you find downloadable fixes?
- Is it obvious how to delete your account and all data and services?
- Do they want your Google credentials? If so, run and bar the door.
- Do they support Oauth? Do they allow you to have multiple Oauth credentials associated with your account? Extra points for each.
- Do they require a security question? If so, they're stupid. (Yes, even Google is a bit stupid these days - but they don't REQUIRE it.)
- If your storing something precious online (ex: backup data), what's the password reset policy? "Industry standard" practices means losing control of your email will cost you ALL your backup data. (for example)
- Can you get your data out in a useable way? If not, run, run, run.
- If there are annual renewals, is there an option to request approval prior to renewal?
- Is there a high quality manual and/or help resource? It doesn't matter whether you're going to read it or not. Products with good manuals are almost always good products. It's a very reliable quality measure.
- Is there a blog? Are the developers proud of their work?
See also: