Comparing business or practice software is harder than it should be, and that is partly by design. Every vendor’s website lists a wall of features, every demo is run by someone trained to avoid the awkward questions, and every comparison you find online turns out to be an affiliate page paid to rank one product first. So here is a framework you can use yourself - the questions that actually separate good software from software that just markets well.
Start with the job, not the feature list
Feature lists are theatre. Every product can tick "invoicing" or "reporting" on a page; what matters is whether it does your version of the job well. Before you look at a single tool, write down the three things you actually need it to do this year - the specific, real tasks that made you go looking. Then judge everything against those three, and ignore the other ninety features competing for your attention. A tool that does your three things brilliantly beats one that does ninety things adequately.
The questions the demo will not answer for you
Watch how they talk about switching
A revealing test: ask how hard it is to leave. Confident companies answer plainly, because they do not expect you to want to. Companies that rely on lock-in get evasive - they talk about "migration services" and "onboarding journeys" that quietly mean "this will be painful enough that you will stay." How a vendor discusses leaving tells you how they will treat you once you have joined.