rookie paint job

I would want to take it down to bare metal. Without doing that, how will you know what's there? You wouldn't want to put the expense of a paint job on it only to have it start bubbling up in a year or two. Also, your new paint may not be compatable with what's under it. Last, I think three paint jobs would have it too thick.
Got a trade or technical school near you? You might check them out to see if they have an auto collision repair course. You might could take a few classes and do the work yourself.
C
Great advice; there is a community college nearby, and I know they have auto body courses. And I hadn't thought of what may be lurking unseen under all that paint. Thanks!

What about replacing the vinyl? What kind of a mess would that be?

I'm still not sure about keeping the color/vinyl original, or......?