I was just talking about this with my mom....
I joined Vortex in 2001, about 6mo after buying my first Corrado. My first round of modifications and maintenance trips were done by a shop that evidently didn't know older VWs.
Shortly thereafter, I met one person off of Vortex, and he introduced me to the man who would ultimately become my Corrado mechanic for about 6yrs and a good friend. I had the opportunity to learn by watching and picking and choosing the tasks I felt comfortable with.
Over the years I progressed to following DIYs from Vortex, and then DIYs on other sites for other cars, and even watching DIYs on YouTube.
I followed a very comprehensive DIY from NASIOC to do the timing belt on my 2002 WRX.
I followed comprehensive DIYs for suspension and brakes when I overhauled that stuff on my Corrado.
I'll be doing the same over the next month as I overhaul the front end on the Corrado again.
Nothing beats the sense of accomplishment and usbesequent euphoria when it all goes back together correctly, and you are neither short parts or have excess.
Currently I am fortunate to be friends with one of the best Corrado-specific mechanics in the tri-state area, and potentially in the country. While I have paid him to do alot of stuff, as often as I can, I watch what he's doing, and try to learn from his work, so that should the same part break in the future, I can fix it myself. By biggest issue is time - my garage is 2hrs away from me, and at best I can only make it there on weekends, and even then, not every weekend.
One of these days, I'll take a week off from work to crank through a multitude of small projects.
I believe anyone can wrench on cars. I apply a similar logic to cooking: If you can read and add, you can cook.
All that wrenching requires is a basic understanding of how things go together and how they interact.
That being said, there are some people who SHOULD NEVER work on cars, and any older car is only as reliable as the person who does the work.