Key takeaway
A feature checklist tells you what a tool can do. It never tells you whether your team will actually keep using it in week three.
Line up any handful of project management tools in a comparison chart and the checkmarks start to blur together: tasks, yes. Milestones, yes. Team roster, yes. Reporting, yes. Almost everything in this category can technically do the basics, which is exactly why comparison charts are a weak way to actually decide, they measure what a tool can do, not what will actually happen once your team is using it.
The question a feature list can't answer
The real differentiator for a small business is not a feature, it is a behavior: will someone actually open this and update it at four on a Friday afternoon, or will it quietly stop being current the way the last tool did. That depends on how much friction sits between "something changed" and "the tool reflects that," and friction is very hard to see on a features page. A tool with fewer features but a genuinely fast update loop, one click to change a status, a task added in seconds, will get used. A tool with a longer feature list that takes five steps to log a simple update will not, no matter how the comparison chart scores it.
A shorter, more useful checklist
Instead of a feature matrix, try this: put a real, current project into the tool's free or trial tier, not a demo project, an actual one, and see whether your team updates it unprompted after a week. Check whether adding your team is a five-minute roster upload or a slow one-by-one invite process. Check whether a task changing status takes one click or a modal with six fields. None of that shows up in a comparison chart, and all of it predicts whether the tool is still being used in three months better than any feature list does.