I telecommute probably 95% of the time now and I work in IT. I pay my own medical. It's nice but you have to be super-disciplined. Honestly, I go to the library a lot to get away from the distractions at my house. If I can offer some suggestions:
1. Work out a routine that you can actually live by. Routine is King if you work at home. Wake up and get dressed, put your shoes on. It doesn't work if you stay in your pajamas all day.
2. Do not stay up late. Do not stay up late. Do not stay up late. Set your alarm for an hour before your bedtime to remind you to get ready for bed, then set it again for your actual bedtime. When it rings for your bedtime, turn off all the lights and go to bed. Proper sleep is, in my opinion, one of the most vital and overlooked parts of working at home.
3. Set daily goals. If you achieve them early, work more to get ahead or else take the rest of the day off. But (1) make daily goals and (2) finish them before doing anything else. Do not take 2-hour lunch breaks. Don't wake up and surf the net, play video games, or do anything else. Don't let yourself get distracted (make a list of your distractions and plans to avoid them). Work first, play later.
4. Have a dedicated place to work. If not a dedicated room, then at least a dedicated desk. Keep it neat and organized. This is essential - psychologically you need a separate place to do your work.
Working at home is both cool and not cool. I do not plan on working at home for the rest of my life. I enjoy it, and I'm to the point where my wife/family/friends let me be (you have to be strict when you are in "work mode" - no chit-chatting on the phone, instant messaging, and so on), but when I have kids there is just no way it will work. You have to be very structured and very disciplined to pull it off effectively. I slaughtered my first month of working at home (January 2006). I've since learned many tricks for working effectively, most of which are listed above. You can fool yourself into believing otherwise, but unless you want to be stuck working nights and weekends because you didn't take care of your work stuff first, follow those rules. The dream of working at home is to lounge around in your PJs, working whenever you want, but that is a big lie. Real work is done in with consistent progress in small doses of focused effort. If you don't focus, you lose. I love working at home, but it's really hard at times. It's not the cakewalk that Hollywood makes you think it is.
Also, it will be harder to get a job online since you don't have a college degree. I would suggest getting at least some certificates in the area you want to work in and an Associate's degree. If you are serious about working at home - especially for an extended length of time - get a Bachelor's degree. Pull out a student loan, take night classes or online classes, whatever works for you. Companies that allow people to telecommute require reliable, educated people that they can count on to deliver. Delivering is all I do - I get my work for week, whatever the current project is, and I deliver. Master your craft, whatever area you choose. I do a lot of websites and also email systems from home, as well as remote administration, training/tech support, and mentoring. It's a lot of work, but it's manageable. The perks are that you don't have to go into work on a regular basis (my work is 2+ hours commuting), you don't have to deal with annoying/mean/whatever people in-person, your time is yours to manage without a boss looking over your shoulder, and if you finish all of your work you can enjoy the rest of the day/week guilt-free. I've had weeks where I've finished up all of my work in the first day or two and have been able to spend the rest of the week with my wife, doing projects, and generally doing whatever I felt like. It's great...as long as you establish the proper system for dealing with your work first as outlined above.