I had a 10 WG and bought a detachable backrest, a wider passenger seat, and tried everything to make it more comfortable for the wife...one trip to Laughlin and her sitting on a buddies Ultra was all it took. I'll admit I was tired of wearing a backpack to haul things around as well. 3 months later the WG was sold and a Deluxe was in the garage. I was happier but she still complained and fussed and I got tired of hearing so now the garage is empty and I'm waiting for finances to get better so can get a Road King....let's hope she'll shut up after this....of not then she just ride anymore! Point is, get something you are comfortable with and like that she will also be comfortable on.....if she's not after that then leave her at home

 

Yep... THAT!

 

Yup, I bought a Sundowner touring seat, quickdetach backrest, and windshield, but it's still not a touring bike. The HD quick detach windshield SUCKS for someone that is 6'0" tall. The wind buffering hits right about the nose level and up. I learned that lesson for 1400 miles.
I tried to teach my sister how to ride when she decided to go out and get a sporty....One of the most exhausting bike experiences I've had. Swore I'd never try to teach someone how to ride. I'm a firm believer in, "either you have it or you don't" I could keep WG and buy an ultra or SG but I'd have to wait 4 more years.

 

Trade it.

 

You will regret it. Get rid of the wife, insist on joint custody of the kid and keep the real Harley. Surely your 8 year old son likes riding on the back of the WG. He'll fall asleep on the Ultra. I went through that with my son and traded my Ultra for an FXSTC and we all lived happily ever after.

 

I went from a sportster to a Heritage then an Ultra.... The Sportster was here for about six months and 2500 miles, The Heritage was a few days short of a full year and 11,500 miles. The Ultra has been here for just under six months and has a few miles over 10,000 miles. Now you can do the math it isn't hard and I am really not in the riding season yet(it has consistenly been over 115degrees here). Yes there is a tremendous difference between the bikes and yes the Ultra Classic has it's own drawbacks, but I wouldn't change from it for any other bike(possibble exception of the CVO Ultra). I guess the answer that you are looking for will depend quite a bit on how much riding you are planning on doing and what kind.

 

I ride about 8-10k a year. Mostly within 100 mile radius, but I do like to take a big 4-5 day trip here and there. The boy likes the wide glide. I think the only reason he wants an Ultra is because of the radio. Wife doesn't ride that much (kinda like it that way to be honest). My biggest drawback for the WG is storage. I can only carry what fits in my pockets. With a solo seat for local riding and I've yet to find a pair of saddlebags that look good on it, I have to wear a backpack when I go anywhere. I've already told the wife that she goes before the HD, but she does have some sway on what kind of HD. haha

 

I went from an 09 Street Bob to a 2011 Street Glide and I know trading was the right choice all around. Comfort and storage is always a plus.

 

Get a "Classic" (FLHTC) and the removable tour pak kit. Then you have the big touring bike and can remove the tour pack and have a street glide as well.

You can also do with with the Ultra and Limited, but the Classic is the way a lot of guys go for "the best of both worlds" bike.

PS - You won't miss your Wide Glide.

 

You will not be sorry to see the last of the Dyna.