You are not asking for trouble at all. It is very natural to want to take your hobby to the next level, and to see if your peers appreciate your work. If people are willing to pay money for the software you write, it means that your software is as good as you believe it is, and outside recognition for success is a great thing. (The same can be said if you have many users if you give the software away for free).
One important element that will effect this that is beyond writing software is the marketing. If no one finds your product, no one will buy your product. While marketing is not rocket science, it is something that requires time and hard work, both in learning how to do it correctly, and in executing what you have learned. The bright side of that is the fact that you will get money for your trouble as compensation.
Figure out if you want to take the time to learn the marketing and sales skills needed to make it work. You can ask the people on this site what it takes (there are several questions on the subject already). If you choose not to take care of the marketing yourself, I would suggest partnering up with someone who would know how to market the software. You don't need to pay this person a salary (unless he gives you a one time consultation) but rather they should be compensated with commissions.