Earlier quoted context omitted.
I don't think customers need to see every feature they request actioned, or even actioned quickly. As long as you're shipping new features and communicate both your roadmap and with individual feature requests, I think people understand. I do, however, think you need to balance big featured with quick wins that make a subset of your clients significantly more happy.
I'm really sceptical about sharing roadmaps. In the beginning, I often talked about planned features, and it often turned out that they took way more time than expected (one of my favorite features is in progress since December 2015). If I share a public roadmap, and then I don't deliver, people will be disappointed. So I've started to only tell people about new features once they are stable enough for testing. I don…
I agree. Your public roadmap should be conservative, or more oriented towards the type of impact you will be making. The intent of a roadmap is to communicate your focus so that folks outside know the general theme. You then have something to reference in conversations later when someone asks for something that doesn't fit with the theme.
Personally I have found any type of feature and expectation discussion easier in person or on a call. I expect feedback over the internet to be poorly phrased or hostile. Expectations break down if you have any type of sales team who are prepared to offer features to close deals.
It looks like you make a database management app for the Mac. If I was creating a theme-based roadmap I might choose a theme like "SQL Console Improvements". You can explain that your focus is on that area of the product, but that your focus may change in the future. When you get close to being certain a feature within the theme will be developed then publish that information. You can operate multiple themes depending on resources.
This approach can also work for feedback. You can let users know that the next theme on deck is "Optimization Tools" ask for feedback on how users want to improve their SQL queries. Then when you start executing on the theme you have collected feedback that can be incorporated. The flow makes users feel involved in the process. Actually summarizing the feedback in public can be a useful community exercise for expectation setting when everyone thinks they have the most important idea.