...Just strange that the only times the belt squeaked after starting, was when the truck was having trouble starting. I can't believe that's a coincidence twice. The belts are new and have been re-tightened in the past month or so.
I'm brand new here, and don't have much of a background in auto/truck systems and repair, but reading this thread and that quote made me think that perhaps you have belts which for whatever have twice loosened over time, causing your alternators to inadequately charge your batteries, ultimately leading to the situation where you experience hard starting. At this point, NOT coincidentally, your belts are loose enough to squeak, which would only emerge upon restarting after the engine has cooled down. Chicken/Egg, Cart/Horse, etc...
I know that with my recently bought M1008, since I changed the glow plugs (only 2 were functional) and other parts of the GP system, my truck has started up MUCH more quickly, requiring only a few seconds of cranking after the GPs cycle pre-ignition. Maybe your GP system is also marginal, as others have suggested, which exacerbates your problem in terms of hard starting, especially in situations where your batteries are not FULLY charged.