We've done lots of split stays. If I'm splitting between CL and non-CL, I'd generally opt for making CL the later part of the trip myself...but you may also temper that by your arrival and departure times. One option we have done if we have a late arrival is to stay some place inexpensive the first night (or last night), then move to CL. You do lose time in moving, but if you pack stregically, then it's not too bad. The way I do it, we do a one day bag..or else we fill a suitcase full of dirty laundry. I also plan our park touring and ADR's around where we'll be. So AKL and Boma/Sanaa/Jiko is good pairing. CR/Poly/GF and the monorail dining, or BWK/BC/YC and area dining including Swan/Dolphin/Epcot's WS.
Disney will move luggage, but we've also found that having a car makes split stays easier, so you an usually leave part of the luggage in the car.
Another important consideration is if youa re doing a pakcage- then you really want to make that the firt part of your trip. You don't want to buy two sets of tickets, and you have until midnight of the day you check out to use up
DDP credits.
For us, CL plus DDP is too much food. Also, my prime reason for picking DDP was to save money. In 2013, it is not priced to save money. You should look at the math yourself, but I think you'll find it a losing proposition. You are most likley better paying oop. Maybe look at deluxe DDP, but that would also be serious overkill IMO.
Keep in mind the new credit card fee cancelation policy too. I tend to go in a large group, and we are pretty eager to keep our signature reservations once we make them, but I hate the idea of a $20pp fee hanging over my head. So we've cut back on meals at places w cc holds.
Whichever part you pick for CL should ideally be days where you plan to spend *more* time at the resort, or at least where you'll take an afternoon break.
CL is a meal replacement for breakfast, just not lunch or a complete dinner.