The fear of committing to a monastic lifestyle I have a persistent fear of going without food that prevents me from giving monasticism a full shot. 

Some background: I suffered for approximately 4 years with something called cyclic vomiting syndrome. This is an affliction characterized by recurrent, prolonged attacks of severe nausea, vomiting, and prostration with no apparent cause. During this time I repeatedly lost and regained 100s of pounds at a time. Losing weight, while something I needed to do, was not fun. My longest single attack lasted a full 7 days during which time I was unable to keep any food down whatsoever, much less get any sleep. Retching on a completely empty stomach 45+ times an hour is a hell that I wouldn't wish on my worst enemies. So, food is important to me. At the same time I realize that too much is not good in a myriad of ways.

So, where are all the Buddhist monasteries at which I'd be afforded the opportunity to practice self compassion as opposed to gritting my teeth and forcing myself through a whole lot of discomfort in order to satisfy my ego and other's expectations of what constitutes a good, chaste and worthwhile existence? That doesn't seem mentally or physically healthy or conducive to showing loving kindness and compassion to others. I'm a firm believer that in order to be able to show compassion for others, I need to show it to myself. I'm mainly thinking about food here. Whatever could be wrong with my eating something when my stomach is growling after noon? At least until my stomach had shrunk to such a degree that hunger pains were perhaps more a nuisance than anything else? 

I think I understand the reluctance on the part of many monastics to allow things like eating after noon, etc. It so happens also, that I suspect that their concern is misplaced. It seems to me that there aren't many things in life that don't consist of shades of grey. It also seems that Buddhist monastics in general tend to lose sight of the nuance making up many of these things.

So, is there a tradition I should be focusing on? A teacher? (Ajahn Brahm is a favorite btw.) Am I way off base with my concerns? If so, how should I go about rectifying my inconsistent views? If not, then what?
By practicing monastic life, if you mean becoming a monk, it's a no go with your current condition. But if you just want to practice meditation, staying at a monastery, you still have to give up Marijuana and Nicotine. No serious monastery would allow you to smoke while you stay there. 

Some monasteries allow lay practitioners to take just 5 precepts and have food in the evening as well. But usually you have to bring your own food for evening meals.

I would suggest for you to do an online meditation course and to get advice on how to give up your addictions while consulting a doctor to treat your ailments without Marijuana and Nicotine.