If I were in your position I would go visit every web development company in your immediate area. Focus on smaller companies, go in and meet the owner, show them you are serious about wanting to follow this career path and ask for ANY crapy part time job they can afford to pay you to perform. If you dont get a yes the first go round, make a schedule to stop by each business once a week. Bring in a box of doughnuts and just check in with them. I guarantee you will have a job at one of these places within a month or two, which is no time at all if you are serious and want it bad enough. Just dont give up, be patient, be persistent. Build a good relationship with the person in charge of hiring and they will want you working with them. Trust me this works, I've seen it happen many times.
A couple pointers:
-Dress professional, figure out how people in the industry dress and make yourself look the part.
-Be on time, screw this up and you will send a lot of time repairing the damage to your image.
-Dont worry about your experience, but put together a nice professional resume.
-Be polite, respectful, and make a really good first impression.
-Read up on a company, it will show you are really interested in what they do and give you something to talk about.
-Instead of paying for more education, at this point(assuming you have a good base set of skills), subscribe to a trade magazine to keep up with the industry. Which again, gives you something to chat about with the owner when you visit with him/her each week.
-Always follow up, always.... stop by once a week and just say hi, show them you enjoy being there. You dont necessarily need to talk with the owner every time, and it doesn't need to be more than a few minutes. just a quick "hi, I was in the neighborhood and thought I would stop by to say hi. Hey did you hear about (some interesting fact about a new program, web feature, etc)".
-Don't worry about pay and benefits for the first job, just get you foot in the door so you can show experience on your resume. When you get this job and have it for a year, then you can start focusing on pay increases, in the mean time learn everything you can.
-Figure out who the sales representatives are in the area for the programs that they use and see if they have any monthly get togethers or classes.
-Figure out if there are trade organizations in your area that meet regularly and go stop by to introduce yourself.
Last but not least, let me repeat again because it is SUPER important... Always follow up, again, again, and again, until someone finds something for you to do in their company. (unless of course things get uncomfortable or they ask you not to). This takes time and effort but will pay off eventually, try really hard to make friends at each place you visit and get to know the people in the industry. Just get involved, someone will notice you and ask you to work for them.
Treat this idea of "finding a job" like a job, you should work at it everyday.