Just my observation and 2 cents worth. On a diesel like the Cummins 5.9 I don't think "break in" is necessarily a matter of the number of miles driven. Yes, I agree there is some break in or run in on the initial start up and hours of run time immediately after but to properly break in and seat the rings and other wear components in the engine completely, I believe the engine needs to be run under significant (not extremely heavy) load. That could be a cross country run with a loaded trailer. In my case, a sugar barrel run (I will load about 3,000 lbs. of sugar) The heavier load will allow the turbo charger to maintain a more even and consistent boost level, loaded egt, and the wear components in the engine will obviously wear differently under significant load as opposed to running empty or no load. Short bursts of high load will not accomplish this and are not even beneficial in the break in process. Gradually easing into a sustained, moderately heavy load on the engine is the best way to break in, in my opinion. Not more than 20 psi of boost sustained and keep an eye on EGT to keep below the 900 degree range and of course and good cross check of coolant temperature and oil pressure is a must in addition to fuel pressure.
Once you have accomplished this you can switch to synthetic since you already have dino oil in the engine. I think break in can be accomplished with either type of oil. Many engine manufacturers are now recommending selling new vehicles with synthetic oil in a brand new engine.