I don’t have a set policy. I research the company and base my decision on the information I can find. For example, Barebones software isn’t a large company but they have been around since the mid 90’s. I may be wrong but Rich Siegel appears to be a person who would have a continuity plan. So I didn’t hesitate to purchase BBEdit for my users and I continued to use it after I retired.
IMO, the ability to get my data out is a must, as is the ability to easily backup and recovery that data. Beyond that it’s just risk vs reward. What am I willing to spend in money and time? What do I lose if I have to start over?
My opinions are frequently a holdover from the days when I had to consider not only my time but that of others. I would try to weigh the value of an app, etc. against the time to replace it and retrain the people who depend on it.
Today I find myself continuing to offer advice based on that same criteria. Or in this case encouraging the decisions of others with whom I agree.