Thank you for your interest. I am happy to share what I found out - I must say I sweated a lot for it. A few ideas:
1- The biggest factor that leads to failure is the social one. I think that even people that would have it easy otherwise can fail because of the surrounding pressure. It is hard to battle day after day with the world, both at the level of cravings and at other psychological levels (such as the sensation of being the odd one out, not fitting with the rest, etc).
Sometimes I dream of how it would be in a society of at least 50% raw foodists. You go out and you see adverts for gorgeous fruits or raw treats; when you feel like eating a bite you easily find a place selling tons of different juices, smothies, raw treats; when you want an evening out you find a nice cosy restaurant serving gourmet elaborate raw dishes; at the mom/baby gatherings the snacks are delicious slices of fruit or dehydrated raw crackers, etc. Furthermore, you have friends that don't think you're a loony when you explain your diet, but share their latest raw recipe.... Dreams...
It all adds up. At first, the enthusiasm of discovering the raw diet shades everything else, but afterwards you beginn to feel either a lonely soldier, a mad case or the victim of a funny, passing fashion.
I am super-lucky that my husband embraced the raw idea too. Otherwise I'm almost sure I wouldn't be eating raw today. I can't imagine how some people manage to stay raw in a cooked family.
The advice I can think of for this point is to find some friends that are at least somewhat supportive of the diet. If real people are not possible, then the forums on the net become vital.
2- There is no universal best plan for the transition, because we are all adapted differently to the cooked diet.
This became clear for me right from the beginning because dh and I had totally different reactions and preferences when we started. He, a sweet tooth, was very happy to jump straight into eating tons of fruits and felt fantastic, as if a weight had been lifted off him. I couldn't eat much, was unhappy and had many points of really hating everything raw.
The key is simply perseverance and trying lots of tips from the many nice people on the net.
For example, I had problems with eating sweet fruits - it was making me dizzy and sometimes fainty. I read that these could mean some hypoglicemia and a temporary solution was to mix fruits with nuts (even though in general is considered bad). I made delicious smoothies and it helped a lot. Later I discovered that the sluggishness I had could be due to too much fat in the diet. I analysed my diet and I was scared to see it was true. I started to reduce it and at the same time increased the amount of fruits and I started to feel better and better. In several months I managed to conquer the unpleasant sugar-related symptoms and was free to eat anything! Now the problem were the cravings and the hidden idea that 100% is somehow incomplete. I stayed at this stage for about 1 year, eating mainly raw but with some cooked additions (such as cheese on salads, roasted nuts, tortilla chips, some meat, etc). After moving to Belize, out of stress, I started to eat a bit more cooked. Then I realised I wasn't really deeply craving or needing that food, so I decided to try a 30 days raw challenge (an idea from Alissa Cohen). It was great and I decided to continue it to see when the cravings kick back in. Well, so far they haven't! (soon 4 months).
I have the impression that everybody, including the famous raw "gurus", overemphasizes the personal experience. I am sure I would have done the same if it wasn't for my dh that had a different transition experience. The trick is to find, among the people that give advice, the ones that were in a similar metabolic situation with you at the starting point and describe having similar problems. All the others might be well intentioned and knowledgeable, but this field is still young and they might be wrong in your particular case.
3- Even though I believe the transition is an individual journey, I think that the "ideal" human diet is more or less universal. Humans are incredibly adaptable, but there still must be one diet that our physiology is best adapted to.
I'm not very sure of what this is, but I excluded from it: grains, all other plant material unedible raw and large amounts of animal products. I think our physiology is a vegetarian one (fruitarian more precisely), but there isn't any proof that small amounts of animal products aren't needed. At the moment I am vegan because I want to be able to produce or gather all my food, and I simply can't imagine killing and eating raw an animal (I can only imagine picking eggs, but they don't atract me at the moment). If this changes in time maybe I'll consume animal products, raw.
So, at the moment we eat lots of fruits in the morning (simple or smothies, juices), we have a giant salad at lunch or dinner, and fit in some nutty meal during the day.
4- It is essential to eat enough. The total callories should not be under 1500, preferably much higher. All the talk about needing less calories when eating raw, etc, does not apply during transition!
If enough raw food simply can't be eaten, then some cooked should be added (preferably towards the end of the day). Otherwise starvation will lead to severe problems (even for overweight people) and the original purpose will be missed completely ("jumping over the horse").
5- Cooked food will always win if given a chance!
Some long time foodists say that in time cooked becomes less and less attractive. Maybe so, but only if there is a strong mental component. At the instinctual level we'll always prefer cooked, as all the animals do.
I am still very attracted by certain cooked smells and dishes, but I just "know" they are not for me. If I don't see or smell them I don't want them.
Minimizing temptations is vital during transition.
I think huge cravings should be given in to. It can be counterproductive to struggle so much.
One trick is to always eat something raw when hungry and not to get to a very hungry state in the first place, by eating something raw on time.
Wow, I've written so much! I hope I didn't bore you to death!
As you see, I'm happy to answer your questions.