How should I decide between doing a PPM Move (DITY) VS. HHG Move (DOD)?

Transportation will have your answers, they will only let you dity if it costs the Army less than doing HHG. If you do a dity and your expenses are less than what you get then you make a little, go over and you pay out of pocket. I personally always went dity except my OCONUS move, and came out ahead. Inquire at the transportation office and they will break down everything for you.

You must decide if you want to risk breaking your stuff, or the Army doing it for you.

But for real, one thing to consider would be the timeframe between arriving on station and when your household goods do.

You may make some money in a DITY, but in my experience it's not worth the headache. If you are worried about certain things getting broken, you can do a partial DITY, rent a trailer and haul your valuables and mattresses. The only time a DITY really makes sense is if you're going to go over the weight. For instance, if you have a boat or a bunch of motorcycles, and ATVs.