I think we can be a bit biased when it comes to any one bike (since they're all fun machines) and it probably comes down to where we're at in our life, health and happiness.

I've owned H-D's since Oct., '74 when I bought my first.....a '75 Gold XLH Sportster and I've owner several since the AMF days.
By far, I put more miles on my '00 Ultra (77,000 miles) than any other bike that I've owned.
I still (and will always) have my '98, 95th Anniversary Edition Heritage Springer and I still have my current "road bike", a '13 CVO Ultra that I really like.
All that said, but considering the price I paid for it, and the amount of time and the amount of miles that I rode it, and the price I sold it for, the bike that I got the most enjoyment out of was my '87 Softail Custom Wide Glide.

A few issues here and there with it and while the newer bikes are definitely more reliable and more powerful now, I'll probably never get as much enjoyment out of another bike as I did that one.

 

My '05 NightTrain. I should be kicked for trading her in for a Coppertop Superglide Custom. What was I thinking?

 

This one:

 

My 06 Heritage Softail. When the marriage suddenly ended, I had the choice of keeping this or the Ultra Limited. I chose the sixth gear. I really did not want to give this bike up.

 

I have had 5 HD's. My favorite by far is the current one, a 2016 Street Glide Special.

 

First HD was a 2005 RK Custom, then a 2007 Ultra, then a 2011 Heritage, now a 2011 Road King. By far my 2011 RK is my favorite, strips down, not top heavy, handles great, no excess heat, good mpg, looks good, bought it with low miles and cheap. It is my last Harley.

 

This one. The day after I bought it in July 2003.

 

14 XL1200T- Great bike to tour on easily and comfortably.

And pick it back upright if needed.

 

Good on you for keeping the springer. I should have had as much forethought.

 

Ah... let me think/? I'm going with the one I have now