The fundamental question is how committed is the team creating the software?
If they are not very committed then don't expect too many updates.
Firstly, Why do people create free software?
Software takes a long time to build and good software takes a lot of planning too, a lot of the free software created is to help the developer get experience. But not all software is built for this reason, another major reason is because it is sometimes cheap marketing. Their is a huge 'consumer eco system' for free software.
I personally use free software all the time but I can handle the quirks and problems when something goes wrong. This is because I experience with programming languages and concepts.
To know if a team of developers is truly committed to the software your interested in, their are a few clues. One is if the software is not well polished then it could be someone's backyard project. Also, do the developers have an active community supporting the project? Is their a support forum? And how often have they updated the software in the past?
One of the fundamental rules of marketing is recognising that no market lasts forever. The principle says that although people's needs never change, what they physically want does. And companies are constantly figuring out how to create a better product than the competition, this then damages an existing products market share.
This is usually a good thing but if your business is committed to using 1 piece of software and then you upgrade your operating system and this software no longer works, then hopefully the developers will make an update, but they probably won't if the software doesn't attract enough attention.
To help you choose if you want to try open source software the video below explains how the 'open source system' works.