A metacomment related to question 6: Ubuntu tells us exactly how many packages need to be updated, and the update is as simple as executing a single command. Th

A metacomment related to question 6: Ubuntu tells us exactly how many packages need to be updated, and the update is as simple as executing a single command. The problem is ensuring that functionality is not broken by things like API or subtle behavior changes. This means that updates end up happening infrequently since they need to be regression tested on a development server before being pushed to production. If a product could solve that problem (classifying updates and performing code analysis to determine if something could break) it would definitely be worth paying for. Note also that you're asking the wrong people, and it's going to be hard to ask the right people with an Internet post. The best candidates for this tool are busy founders/CTOs/sysadmins/engineers who don't have time to manage their updates, much less take surveys on Hacker News.