If you are going to mess with free software, there are some usual software concerns you are used to looking at including being careful to make sure the software runs on your operating system and within limitations of your computer's memory and other resources.
Other good things to look for include a steady home page maintained by the programmers, documentation, a lively community of users. If you pull anonymous software from people's emails or third party sites, you risk harming your computer with malware. You don't know where it came from or where to find the programmer if you have trouble. For these reasons, look for free software that has an actively supported website. Learn about bugs, expected new features in the upcoming version and be able to ask questions if you have problems installing, using or removing the software. It will usually bring together resources supporting your software.
Documentation is also a very good thing. Whether they are in the form of an FAQ, tutorials, in depth manuals or videos these will be helpful. Even with the simplest programs, the programmer's choice of keys that activate features are not obvious. For large, complicated apps you will probably need as much in the way of textual educational tools as you can find. If your software goes mainstream, you may even get independently published books.
When documentation fails, it is essential to be able to contact people who may have answers and be able to calm us from a panicked state. For small projects you should be able to at least contact the guy who wrote the program. Larger projects or projects that have been around for a while may have user communities that could support any of a variety of tools such as blogs or email lists. One form of support you will be unlikely to find is phone support. We are talking free software after all.