bought an 08 ultra brand new and as usual put lots of $$$ into her. as time goes by wondering if its time for letting it go and stepping it up a bit. course I would have to convince the wife. how much better are the newer models?

 

I have an 06 Ultra and I'm sticking with it. Lots of upgrades done to get it where I want it, and its paid for. The new ones are nice, but not $$$ nice IMHO. Next up for me is installing the Progressive tour link.

 

I should mention she only has 21000 on her thundermax 551 cams new 944 in the rear and plenty of chrome but seem to get an itch once in a while and also paid for.

 

07 & 08 don't have the best rep but you've undoubtedly heard that before. Having said that I bought an 07 about 18 months ago and love it.
A buddy of mine has a 14 limited and it does have some improvements. I've ridden it a few times for short rides and there are things I like about it and things I don't.
Is it a big enough difference to spend that much money? Not for me right now. Maybe in a few years I'll consider a used one but for now my Ultra with stage one is more than adequate.

 

Keep it! I love my 08. Has almost 60K miles on it. I just got it tuned for the engine the previous owner put in. Been a bit of research and learning actually.

I would say just go buy something "different" Maybe your itch would be scratched by a dyna or softy just for putting around and still afford you to keep the 08?

 

Have her sit on the back of the newer touring models. My wife climbed on a 2016 Road Glide Ultra and said it was significantly more comfortable noting more space, better leg position, nicer arm rests in particular. I am going to let the ESP run out on my 2010 before we go that route. Harley claimed the passenger experience was improved in the new designs. My wife confirmed it.

 

Dump it. The post '14 bikes are sooo much better. I really liked my 105 ann ultra. It was a huge improvement over my '03. Wasn't impressed enough to dump it for '09-'13 due to my loss I would have taken. These new bikes really are nice and I wouldn't go back.

 

My '07 with 53K, after a few recent performance mods is now running better than it has in its entire life. I have no desire to part with it.

 

You could always rent one for a weeded and take the wife on a trip. If she doesn't end up hinting to get one afterwards, it might be hard to convince her later.

 

buying a new passenger seat, footboards and backrest/armrest is a lot cheaper than a new bike... unless you've got $20 grand burning a hole in your pocket...