my two cents...i actually don't see anything wrong with him doing 1200-1500 calories for the first 4-6 weeks....when you're that big, your deficit can be more dramatic without taking a toll on you (for a short time at least). he has more than enough stored fat to compensate for the decrease in energy. now whether he sticks within that range is another thing. but between the quick results (encouragement) and training himself to feel fine with less, dude can easily tackle a more sustainable phase (1800-2000 cals or whatever). and dropping 20lbs off the bat will make a world of difference to his ability to workout (whichever type of exercise program he decides).
i also suggest you go into this with training wheels meaning, if you have classes at your gym or you're willing to drop $20 on some bootleg beachbody DVD's (or d/l them), then build classes or DVD workouts into your schedule. i don't see a lot of men doing this and yall are missing easy, fun ways to get 45-60 minutes of cardio. cardio doesn't need to be boring shyt like mulling away on the treadmill and elliptical for a damn hour, and at your weight, HIIT might be too intense (and if high impact, bad for your joints).
go to kickboxing, spin class, body pump, bootcamp, etc. or do an online/DVD workout ~4 days a week. you don't have to figure anything out, just follow the workout and work your hardest. treat it like work or school, that hour becomes immovable - don't switch the plan for bytches, not to get high, not to pick up your brother from across town, not to go home and watch tv, etc. supplement this with a few walks per week (or even taking a 10 minute walk every 2 hours at work....that's ~40 minutes of walking right there).
lastly, i'd also suggest building a meal plan...tons of ways to go about it/resources available online, but for me, having a plan is immensely easier than just winging my way to my calorie target.
you said you eat out a lot which means you don't cook, but there are ways around that...there's so many precooked/preseasoned meat options (if going this route, don't salt any other food in your meal as these meats tend to already have a decent level of sodium), shouldn't be hard. it takes ~5-10 minutes to steam or sautee some veggies or grab a handful of lettuce out a bag, drizzle it with some olive oil and lemon juice and call it a meal.
and learn what a serving size is...really. i'm surprised at how many people ignore/don't know this.
you won't lose weight without effort and commitment, but the more you structure you give it, the easier it is IMO.