I just traded-in my 2014 500L Trekking, so I will no longer be visiting the forum regularly. My trade-in was not because of any mechanical issue, but simply because we needed a bigger vehicle. I purchased my 2014 as a new car in March of 2015, and between then and now, I only ever had ONE problem with it: The battery died after about 2 years. (Replaced it with a Duralast Gold.)
IIRC, there were two major TSBs for the 500L right off the bat in 2014, one was the DDCT reprogramming, and one was a battery drain issue that stemmed from the TCM (or something) still drawing power even when the ignition was fully off. All TSBs had been applied by the time I bought my particular car, and as I said, I never had any issues with the drivetrain.
My 500L had low miles due to my short commute, but I loved driving it, and it remains my favorite car that I have ever owned. But I'm not gonna lie, I would have definitely started to worry as the miles racked up. I would recommend this car to anybody, but it would need to be a 2015 or later model with the Aisin, for sure. I loved how the DDCT drove, but at this point it just seems to be way too big of a risk to own.