I lost most of the weight I needed to lose before I went grain free, then I lost a couple more kgs afterwards, but the big advantage to me is that LCHF makes weight maintenance very easy.
Eating out isn't a huge issue as long as you're not in a restaurant that is really carb heavy - I find the worst places are coffee shops and canteen type places (hospitals are the very worst). Most restaurant have reasonably LC meals as long as you're prepared to tell them no bread, fries, etc. I have cut back a lot on eating out as it's much easier to avoid grains if you're making food from scratch.
I'm a very basic cook and don't find myself getting bored with real food - though some people seem to get obsessive about always eating new recipes. Doesn't bother me at all eating the same foods time and again. I think my attitude to food has changed a lot.
The biggest issue is learning to read food labels - I avoid most processed food in general, but anything I do buy, I'm very careful to check the labels. It's scary how many foods have wheat, corn, sugar and soy (which I also avoid) in the ingredients! Even the most unlikely foods like salad dressings.
Very early on I read a quote from someone to the effect that there is no food I like more than I like my eyes - and it really stuck with me as motivation.