You say you are self taught, but if you don't have a degree and certifications that's really going hurt you in the eyes of HR. College doesn't necessarily teach you the tech skills, but if can help you develop the skills to work with other which you will need in your professional career. I'm also self taught, but I went to school. I honestly learned more from my part time programming job I had while I got my bachelors than most of the actual courses, but the later courses taught me interesting things that have come in handy when trying to come up with creative solution to some complex issues.
My experience with people who haven't had formal education is mixed, some of them are brilliant, some are idiots who think they know everything, and the worse are the people who fall in the middle. These cowboys can come up with incredible solutions, but they rarely think things all the way though which can lead to critical systems breaking at the wrong moment which can cause days or weeks of downtime.
I'm probably around the same age though I might be a little more end of Gen-X. Even with a degree and experience, getting a job is extremely difficult. I've found it hard to pass through HR, but getting in front of the actual IT managers and developers would allow your knowledge to shine. The problem is getting there, you are right about needing industry contacts. The best way to get these is networking. Look for user groups in your area and start showing up. A lot of the people going to them work with the technology in their day to day jobs. Talk to them and impress them with your skills, they might be able to tell you about a position at their company, or one a headhunter has been stalking them about.
Try seeing if there are any small/medium consulting firms in your area. Working at these allowed me to get hands on experience with a large number of technologies, as well as developing a large number of contacts with both clients and fellow employees. With a small/medium business you'd have more luck getting in from of a decision maker and getting to show off your knowledge. I was able be at one company while bouncing around different projects as I was needed. This gave me exposure to an extremely diverse number of technologies and environments without looking like I was job hopping every few months.
Finally don't rely on job postings. I was only ever hired at a single place by replying on them. My other jobs were knowing people who could recommend me, or with my latest using a recruiting firm. Try directly contacting a recruiting firm and see if you can get a meeting with a recruiter. This will allow you to discuss your skills and put you at the top of their call list when something relevant opens up. It will also give you some interviewing experience. Just be blunt, let them know that you are having issues in your job search and any advise or critiques they can give you are welcome.