Monetizing, the Psychological Prep First
You have your wonderful OS project which is slowly changing the world. You also followed my advice and established a nice web presence with a lot of site stickiness, a strong community, and good inter-activity. So, it looks like you are in a good position to start earning some financial rewards for all that hard work. I am going to outline a strategy, but first you are going to have to sit back and read my musing on a related topic.
You as a developer, and as a web publisher need to know that there is no shame in wanting to pull some income from your project. It is a noble profession! You are truly doing something that is making the world a better place, and you should at the very least be able to survive while doing all this good. So, if you have any guilt from wanting to do this, you need to let it go.
Do you believe in your project? Good! Then think of this as a way to ensure your project will thrive. Without taking care of your own basic needs you will not be able to take care of your project the way it deserves and the way your use base will come to expect. In fact, the ultimate beneficiaries of your monetizing your project is your user base, because they will be the ones who enjoy the improvements which you will be able to make because you will be able to dedicate yourself to the project more fully.
If you agree with me then you need to not be timid about your intentions to monetize your project. Don't try to hide it as if you are doing something sneaky. You will need to be bold if you want to succeed.