By necessity... like others say, get a junker, but make a pact with yourself to DRIVE it
If it breaks, fix it... if you're in over your head, you still have your good car as "backup", and it's around if you need to take others along or go somewhere nice.
"You mean you can actually *FIND* the gahdamned motor under all that plastic *expletive deleted*it?? Better man than me....."
Yup, first thing I ever worked on seriously was an '84 Thunderbird 3.8V6 with Ford's EEC-IV computer. It was actually pretty simple, the computer generally tells you what it sees. Now, that's not saying the same thing as it telling you what's wrong, it just knows what it sees... but it's a good clue, and usually it'll spot something for you before it becomes evident, like an O2 sensor becoming slow.
I've also worked on a '69 F100... single point distributor, autolite 2100, simple as simple gets. It was satisfyingly simple but still needed constant attention due to age. There are tricks to the old stuff that you've got to keep in mind while you're doing something, like making sure dwell is set right before attempting to fidn the right jets, making sure the carb is nice and clean before adjusting the idle circuit, wondering if the timing advance springs are fresh enough to work properly, what timing chain stretch can do to you and how to find it on the vacuum guage, etc.
Frankly, reading "420: emissions out of spec, running rich" on a code reader works a bit better than driving along not knowing anything's wrong till the exhaust is choked with carbon or you note a whiff of gas vapor in the exhaust at a stop, or noting it takes a few moments longer than usual to warm up, or economy's dropped by 1mpg, etc. etc.