I was told enlightenment frees you from craving/aversion. Just curious to what degree...

Assuming Chogyam Trungpa was enlightened, it could not help him get over his alcoholism.

And cocaine use apparently. Could it be that Trungpa got himself quite advanced on the path but got stuck in some heavy dark night and never really made it to Arahanship?

Ajahn Chah was known to smoke and chew betel.

Craving/aversion arises and passes away, but the question is to whom does it arise and pass away; the degree would be how much self is there to experience it.
I can tell you that the emotions around urges become less sticky along the path but thoughts still happen. It's the doing that counts.
Shinzen Young has some info about his stopping "After one ten-day course in the U Ba Khin tradition of body sweeping my ten-year addition to marijuana simply vanished without any on the wagon-off the wagon." link
In his case it was just a retreat that did it for him....

Not to hijack anyone's thread, but what about phobias? Mine are still alive and well. That's aversion, I know , but for all this stuff I'm wondering why some things stay and some things go, and when (not to mention how).

Here is something that I liked from the end of "In the Realm of Hungry Ghosts" Its lifted from an OCD treatment. I shorted it the the salient points.

Label the addictive thought or urge exactly for what it is, not mistaking it for reality. “I don’t need to abuse a substance; I’m only having an obsessive thought that I have such a need. It’s not a real, objective need but a false belief. I may have a feeling of urgency, but there is actually nothing urgent going on. Conscious attention is the key for physical changes of the brain.

Urge surfing meditation also helps.
You don't need enlightenment to succeed in rewiring your brain to incrementally make it better and even if you don't eliminate urges completely just turning down the volume knob til it's lessened and quicker to fade is pretty darn good.

Phobias, hmm. I guess it could all apply but I'm not knowledgeable in that area... I'd still say that the emotions associated to a phobia would be less sticky and that you can rewire your brain, but that is just my opinion.

I know a handful of people who were spontaneously cured of addictions during the A&P, the one good friend from cocaine, one peripheral acquaintance from alcoholism, one person I met briefly while traveling from marijuana addiction.

Hm. Totally can't get the youtube video I want to show you to link properly.

Go on youtube and search "yuttadhammo addiction" and you'll find some answers.

interesting question, there would be the bodies "craving" for a level of chemical that it is use to and those feeling feed thoughts that this produces. How many people that claim enlightenment still smoke cigarettes. As a smoker I have contemplated and investigated the physical and emotional sides of withdrawal. This still has to be craving and aversion. I could go days without a smoke but there is an ingrained habit of having something in my hand in certain situations, such as after a meal, walking from the train station on the way to work.

Could an addict or someone with drug cravings be in a position to support the kind of practice that is needed to reach enlightenment?

First, the idea that someone goes on a retreat, or crosses into a specific stage of mental training and is abruptly free of their chemical dependencies is fanciful, or at least speaks to the lack of severity of their addiction.

If you're talking about drugs of physical, neurogenesis-style addiction, such as acute alcoholism and/or benzodiazepine addiction or opiates, or even more crippling addictions like intravenously using high quality opiates, you're talking about serious changes to brain chemistry - the longer the use, more serious the changes.

You're talking about shot-out reward centers, dopamine that won't show up, too much glutamate releasing, basic fibroblast growth factors, and a host of other stuff that reasserts the feedback loop of craving and relapsing and addiction.

All this takes years to work through and my guess is, thanks to neuroplasticity and the fact that you can rewire your brain, and the fact that fMRI's and other brain scans are so far showing that meditation increases the production of chemicals that get depleted while in addiction, you'll find peace from the fiending long before you get enlightened.

Please keep in mind, what we know about addiction from a brain science perspective is little. What we know about enlightenment or the neural changes in the brain while sitting is even less.

Buddhism attracts people recovering from addiction because it speaks directly to the end of craving and who wants an end to craving more than junk monkeys and crack monsters?

But don't let a loaded word like enlightenment and your ideas about what it might or might not do to your relationship to the get-high interfere with you using strong practice techniques to deal with THIS moment, to deal with THIS craving.

yes

There are too many maybe's to answer this question well
What drug? what frequency? how long have they been doing it? Is there a support system to allow practice? and many other factors apply to the probability of success.
Enlightenment? Do you mean stream entry or 4th path?
It's like asking how many negative aspects can be stacked before stream entry is unachievable....depends on the person....
I stalled out and had to give up beer completely to get things going after stream entry..