Let me give you my experience.
Calorie counting, at first, is overwhelming. Some tools can help, like
www.fitday.com. Using that, especially, is tedious at the beginning, because you have to input the nutrition labels for all of the foods you eat regularly. Once you have it down, though, you'll find it goes a LOT faster than you imagine it will. Currently, it takes me about 10 minutes a day to plan and track all of my meals for the day. I do this for my partner as well - but its easy, I just make her eat all the same things that I do.
If you have a picky eater, calorie counting allows you to eat things he enjoys while still staying on plan.
It can been overwhelming, absolutely, to start counting up those calories. Until you get comfortable with the tools, it is not so quick. But I -promise- that it gets a lot easier, and it makes the weight loss thing really straightforward, at least for me.
I'd suggest that you try it for maybe 3 weeks. Thats enough time that most of your regular meals and snacks should be inputted and you'll be used to the software. Now the first three weeks, this is going to eat up some time. But after that, really, it won't - and it will be habit.
If you find you are cooking the same things over and over again, from the same recipes, you can input the nutrition facts for the entire recipe into a "Custom Food" on fitday. For example "Fiance's Favorite Meatloaf" would be a custom food. On days when you cook that, you just add that custom food into your day - takes less than a minute. Again, once all of the information is in FitDay, its super fast to work out your days.
If its really overwhelming or you, though, and you have the financial resources to do so, you could try out a meal-delivery service (nutrisystem, ediets express, or others) - but that might not work out well with your picky eater.
Best of luck in finding the plan that works best for you!