If I had a time and youth machine, I wouldn't relive my life exactly as I have, that would be boring.
I know, that's not really what you're asking.
If I was about to finish undergrad now, I'd still probably go to medical school. It may not be the sure path to wealth it once was, but it's still a sure path to a secure and high paying job that, oh by the way, is interesting rewarding and useful. I'd make a point of going to the cheapest state medical school I could and minimizing debt.
I'd still do anesthesia because the actual job is wonderful. I'm not sure I could gut out an IM residency to get to cardiology on the other side. No desire to be a surgeon. I might be able to do path or rads. Anesthesia fits me perfectly.
I really don't fear CRNA competition, or unemployment, or the notion of salaries cratering to primary care poverty levels. There are worse things in life than making $250-300K as an anesthesiologist, though sometimes you wouldn't know it by reading this forum.
I think the notion that the average (or even above-average) med school matriculant could have just as easily rolled over into a lucrative i-banking job or tech startup or other entrepreneurial rocketship to wealth is one of the more laughable grass-is-greener recurrent SDN fantasies. Brains and hard work will get you far, but those fields are littered with the corpses of also-rans.