I know you can ask for recommendations based on the criteria you give, but can I ask whether a game/program I've found will be right for me based on what I want from it? For instance, "I found this program, I didn't like a program similar to it for these reasons, I like these things I've heard about the program." Is that allowed on this site?
Great question. It's definitely a gray area.
My interest is to help as many people as possible, so therefore I would like to see every question on-topic. But because of the current layout of StackExchange, this is not really possible. Personally, I often wonder if SE would be better with only tags instead of many separate sites. But I digress...
Instead of asking if a software package is "right for me", you could definitely write "these are my requirements, and I tried package XYZ and I didn't like it because of these reasons" (and then list the reasons).
Although I don't want to say it, I think asking "is software XYZ is a good fit for my requirements" (and then listing the requirements) will be considered off-topic by our community.
That said, what is considered on-topic and off-topic is not written in stone. Instead, it is defined by the desires of our community. As an elected moderator, I'm very willing to go with whatever our community prefers. Personally, I prefer your question to be considered sufficiently on-topic, but I think I'm likely in the minority.
Conclusion: You ask a great question. I think it's worth hearing what the rest of the community thinks.
P.S. Izzy has to buy us all a free drink when he posts that he thinks it's off-topic. :)