I agree with bensummers. It is not about being a dick, it is about being treated fairly. You have been severely underpaid for a long time, and he acts like you can't have a life of your own but just be a robot-like jack-of-all-trades.
If my boss didn't pay for my health bill and asked me to work while at the hospital I would definitely not let it go like that, you are a human being, moreover, you are helping him to get money. And you are almost getting no money back.
As about lawsuits, it greatly depends on how you focus it. You are being exploited, you know it (and he knows it). You could probably sue him right now. And telling your colleagues about how work was like there is not unethical, nor illegal, it is helpful for them.
Couldn't you just balance on paying for more bandwidth (don't know the prices where you live) with just more freelancing? When you say "bills" you mean just that, or include expenses like food and the like?
Sounds like my gf's work, where people expect to get a Facebook like where users post the content and they don't need to do anything, for a bargain price. It's a sad state of affairs, and teaching clients is a no-no, because a) They don't get it b) They may not hire you
I do agree that my colleagues do need a little guidance in the situation as well. They are almost all new-hires right out of college and were never exposed to anything else.
With bills it comes down the items I listed before (housing, car, student loans, credit cards, utilities) Food/misc wasn't included.
The issue with this area is it's fairly stuck in the old' days. People expect to pay $200-$500 for a website, regardless of what it does. It could be one page, or it could have all the functionality they would ever dream of but only expect to pay a one-time fee.
Just a thought, but have you considered that in your freelancing you might be aiming at the wrong market?
You say that people expect to pay $200-500 for a web site, and I'm sure a lot of places do, but that's the same everywhere. Some places want a cheap site that a college student could do or that they can outsource to someone they'll never meet in a low-paying country. Naturally, the quality of what they receive will usually reflect the price.
On the other hand, you seem like a diligent person and you seem to have some real skills in this area. You might want to consider aiming at the higher end of the spectrum, businesses who see a web site as a serious investment, and will pay accordingly for someone who is going to do the professional job that a typical kid won't. Look for the projects within reach of one person (give or take outsourcing any areas where your expertise is lacking) over a few months, and with the five- or six-figure price tags.
You don't need a lot more hours or a large team to take on these medium-weight jobs, but you do need a professional approach as well as the technical chops, and awareness that web development involves things like usability, accessibility, branding, etc. as well as just hacking on HTML. It sounds like that's exactly the sort of wider awareness and business-like approach that you have, but you'll never make the most of it picking up jobs for peanuts.
If my boss didn't pay for my health bill and asked me to work while at the hospital I would definitely not let it go like that, you are a human being, moreover, you are helping him to get money. And you are almost getting no money back.
As about lawsuits, it greatly depends on how you focus it. You are being exploited, you know it (and he knows it). You could probably sue him right now. And telling your colleagues about how work was like there is not unethical, nor illegal, it is helpful for them.
Couldn't you just balance on paying for more bandwidth (don't know the prices where you live) with just more freelancing? When you say "bills" you mean just that, or include expenses like food and the like?