See below:

https://carkiller.com/scottykilmer/qa/new-honda-pilots/#post-79304

https://www.cashcarsbuyer.com/do-honda-pilots-have-transmission-problems/#om

https://www.motorbiscuit.com/the-most-complained-about-honda-suvs/

https://www.carparts.com/blog/honda-pilot-reliability-and-common-problems/amp/

(3rd Gen)   https://www.motorbiscuit.com/the-2016-honda-pilot-had-an-alarming-number-of-transmission-problems/

Also, realize the 2nd generation (model years 2009-2015) with the 3.5L V6 engine (J35Z4) has port injection and is not a GDI engine - a good thing for maintenance, repairs, and longevity.  The 3rd generation (2016-present) has a GDI engine (J35Y6) with no port injection so overtime can be susceptible to carbon buildup on the back of the intake valves (need catch and cleaning back of intake valves to mitigate the issue).  Your year 2014 - 2nd to last year of that generation with some of the bugs/issues worked out - seems to be one of the better years of that generation.  To make matters worth, the new Honda Pilots now come with a complicated 9-speed ZF auto transmission and long term reliability on that is unknown (but most likely not going to be as durable as the 6-speed).

In short, I would stick with the devil you know.  Although realize 2nd or 3rd Gen - both engines have cylinder deactivation (what Honda calls VCM) so I would disable it sooner rather than later to avoid potential issues down the road.  Also, be sure to change engine oil every 5,000 miles (especially if you keep the VCM on - needs clean oil) and stay on top of the transmission fluid changes.

The 2nd Gen Pilot is my favorite Pilot. Take care if that baby, and she will treat you well.