Good question. I'd like to study and come into a Help Desk job or something like that. What's a good STARTING POINT and what's a good expectation in terms of completing certain BENCHMARKS? Just what are some different PATHS in the field (ex. Security, Hardware, etc)??
I'd like to GUAP LIKE A DOG
while still working independently and on my own schedule?
You're probably not gonna start out making bread like that. Like any other industry, you have to start at the bottom and pay your dues. If you don't have any experience/degrees, I'd say study for your A+ and take the test when you feel like your ready. If you need help, there are guides on the Internet as well as A+ prep classes you can take at many community classes.
Once you have your A+, start applying for Help Desk jobs. I probably wouldn't worry about other certs until you have some sort of experience. Depending on where you live and the job market in your area, you'll probably be able to apply for jobs paying anywhere from $12-$16/hr. Once you get your foot in the door, start looking into other certs and thinking about specializing. I'm still trying to find my own path in the field but there are lots of different areas you can specialize in...networking, servers, security, virtualization, infrastructure, Linux, etc.
If you're serious about going into IT, it may also be worth checking your local community college to see if they have any two-year IT programs...it's easier to get your foot in the door (with no experience) if you have a degree or at least have passed some IT classes. Last few IT support jobs I've gotten have required at least a 2-year degree just to avoid having your resume thrown out.