Your BIL's diesel as would all newer diesels with current emissions systems suffer from his short commute. As a mechanic I would think he should know that.
The dealer will not be able to fix it. But a 15 minute instal of a tune such as GDE's that essentially defeats the EGR will. And it will get measurably better economy pick up enough power to feel it in the seat have less emmissions problems last longer and cure male pattern baldness. At least it did on my ED & I have a full head of hair. 252,000 on my ED so far.
A WDH will likely have it tow that trailer extremely well. BTW a tune like GDE or PPEI can add a software driven turbo brake which is a great benefit when towing. Mine can hold & control speed up to a 6,000 trailer pushing me down s 6 percent grade. I'm sure it in part is why she still has the original brakes.
Now that I have identified the problem for you and the fix you can stop sitting around. Maybe you can buy your BIL's for cheap then when you talk about it in the future he can kick himself for selling it. BTW did I mention mines uses less fuel than the beater 4 cyclinder car it replaced. Unlike yours 30 mpg hwy is something a Hemi jeep will never sniff. Don't get me wrong I like the Hemi & getting 0 to 60 quicker but I like my own cash better. Best of luck whatever you decide.