I have not yet had my surgery, but I have done a lot of research, spoke to a lot of people, and had a lengthy discussion with my surgeon about some of the issues you mention. So I'll share what I have learned and the advice I've been given.
Having read a lot about the diet restrictions I worry that not having good mental control over my eating behavior could cause problems. Mindless eating by its nature is uncontrolled and I wonder if others have found this problematic and if so how did they deal with it.
My surgeon has instructed me to eliminate ALL distractions during meals to avoid mindless eating. No eating in front of the TV, while driving, or at the movies. This will certainly take some time to perfect as you have to change your mindset but it is something that has to be done to achieve willpower over mental cues/habits.
Are holidays and special occasions ever the same post surgery? The euphemism "pigging-out" is actually something pleasurable beyond just food. For example most holidays and special occasions have a component of overeating. Almost seems that once you have the surgery those pleasures are a thing of the past. How do you break this or is it always a struggle? I've been thinking a lot about my favorite holidays (i.e., Christmas, Thanks Giving, Fourth of July) and in my mind I hear "Maybe I should just try a conventional diet program again at least I'll still be able to enjoy turkey, mashed potatoes and pumpkin pie at Christmas".
From people I have spoken to, holidays (and any meal really) is significantly different for two reasons: 1. The obvious that your stomach is now teeny and cannot hold nearly the capacity it once could and overeating can lead to becoming physically ill thereby teaching your brain that overeating is no longer a pleasant activity and 2. Due to the reduced amount you can eat and feeling fuller sooner, people have told me that food no longer runs their life. They have stated that where they used to be either eating or thinking of eating, their brains have shifted because the body doesn't need (and in some cases doesn't crave) food the same way. They now eat to live rather than live to eat.
I travel a fair amount for work. I have actually delayed the surgery until summer when my travel and speaking schedule slow for a few months. I am scheduled for surgery the third week of June which is three weeks after my last trip. Then I don't have anything else scheduled until early September but that is in Europe. I have read a lot of posts but I have not found many that outline traveling success recommendations. While there is some entertaining in the mix it is not excessive I am more interested in how people manage a restrictive diet around the chaotic schedules of business travelers.
You may need to adjust your eating schedule to work around your travel, but the same rules should apply where feasible: No distracted eating, no snacking unless unavoidable, when you do eat choose protein first, and stay hydrated.
Last but not least. One of my bucket list items has long been to ride a bicycle across the country from coast to coast. Before I even contemplated the surgery I started making plans for when I might be able to do this and how I could go about making it happen. One of the big issues was certainly my weight which would be helped by the surgery. However, again with the diet restrictions and hydration needs I wonder if there are any challenges or problems with long endurance activities like this. Currently this would be a couple years post surgery so healing should be complete, my concern is are there problems with dehydration.
I haven't researched this particular topic, but several years out it seems like many have returned to a "normal" diet. Not back to overeating or eating poorly, but eating reasonable portions and drinking reasonable amounts of water. In this regard, I imagine the risk of dehydration would be lessened so long as you aren't going all day without some form of nutrition or hydration.
You do seem to have a lot of mental obstacles to overcome. You could certainly benefit from additional therapy before and after surgery, possibly by a therapist experienced with food addiction.