OK, I guess I will take the role of "devil's advocate". Having owned 2016, 2017 and now 2019 Tri Glides, I have found the performance and comfort enhancements "somewhat" worth the added costs of ownership. I really, really like my 2019 although I only have 1400 miles on it. The latest M8 engine seems ideally tuned for the mass of the TGU. The suspension is better than it was but could be better and I think aftermarket strategies like DK's have proved to be quite well received.
The 2019 is just a more pleasant ride and recently, I found that the changes in suspension are more readily felt in a two-up condition. Just remember that there is about a $7k profit margin in a new TGU and that is what is allowing the dealership to give you more than you paid for your current ride. On my 2017 that I had bought used with 90 miles, the screaming deal that I got on it an my 2016 new allowed me to get into my 2019 at a fairly favorable price in terms of real dollars.
Only you can decide how best to spend your discretionary monies. If you have other burning things to blow dough on, then the upgrade may be less interesting? Can't wait to hear how we have spent or not spent your money:clapping: