I've felt the exact thing in my handlebars my front-end definitely felt light I checked my air pressure and it was set at 36psi front and rear I changed it to 40/40 and things got better..... I went from a completely stock ride to adding a 23/17 setup and a King tour pak

 

The larger front wheel changes the geometry. I went through this with an 08 Street Glide with a larger front wheel and adding a tour pack.

I would suggest getting Rid of the stock rear shocks for good coil over suspension, and would go with the 13 inch to raise the rear up.

 

I have the same light front feeling on mine, especially when you get on it hard. Mine is a 16 Road Glide Special..21/17 Extreme Machine Combo-Progressive drop-ins with 1" lower set up...was even more pronounced with the front forks at stock height.

 

Thank you all for the input. I think I/we may have figured this out. As Cosmic Razorback and a few others said, the geometry is now different due to the larger front wheel. It is close to stock but not quite there. The added weight from the tour pak suspended out over the rear is lightening up the front end even adding to these symptoms.

So before I headed for a long ride today, I realized what could be the main factor. I did not have the rear adjustable suspension adjusted correctly. I had it set for a 220 lb rider, aka me when I bought the bike, and nothing more. Add the 120lbs. from the wife, the extra weight from the new tour pak, and the SGS premium shocks not adjusted properly, resulted in an already slightly out of whack from the wheel package to becoming a severely out of whack SG due to the badly sagging suspension making the bike even more lower in the rear. I adjusted the shocks to accommodate the extra weight and the tour pak was barely noticeable. Rode all kinds of twisties and turns with no issues other than this back tire thing I deal with.

Not sure how to explain it but I get a severely raised center contact area on the rear tire as if the center of the tire grew or is coming separated from the rest of the tire. This is my 3rd and all three did the same thing (i'll attach a picture). Not sure what to call it but I have no idea what is causing it. Constant extra weight from riding 2up? Incorrect pressure? Is this common with 200mm or over sized tires?

I am on my second front tire and I have about 3k on it now. I don't believe it is contributing to the problem in any way.

 

If that "ladies wallet" is like my wife's purse, YOU'RE OVERLOADED!

 

I just got back from a long trip, 2 up, tour pack, rack bag, and loaded to the max. There were a few times where the front end/bars started to shake/wobble. It was always at very slow speed, while turning, pulling away from a stop, or slowing to a stop. I contributed it to all the weight on the rear end. I was worried at first, but my cousin had the same issues with his dyna while riding right next to me.

 

Ditto on changing rear suspension,,,Those "premium" shocks are anything but premium. I have a 15 SGS with a 21/17 Performance Machine wheel setup with the tour pack. I also ride two up about 98% of the time. I just changed to the Legend Revo 13 inch shocks about a month ago.....night and day.....unbelieveably better ride.

 

I have a king tourpak and do not the issues you are having either. Check your riser bushings, when these are loose it causes the front to feel like the axle is loose. Also, the wear on your tire is very unusual. I don't know what would cause that but my first rear tire had the same issue. I got a Michelin Commander II and it's wearing much better. That will cause a lot of hum in the corner but I never noticed that it felt light or loose in the front.

 

You didn't say the year of your bike, but I would guess that it's a pre 2014 because wobble you describe was fixed with the 2014 upgrade. I had the exact same experience you described with my 2009 Utra, but not my 2014. If your bike is 2014 or newer, than I have not experienced it with my 14 Rushmore limited, yet.

Beary

 

It's physics, any weight added above and behind the rear axel adversely affects handling. The further away from the axel, the more affect it has, like a lever and fulcrum.
Another issue of adding weight is lowering the rear which changes the front fork geometry. That's why adding pre-load thus raising the rear helps to restore handling. IT CAN NEVER be the same, it can however be acceptable.