Without a way to get the bike up high enough,it would be a true pain.With it up enough it is not bad at all,after you do it once you learn all you need to.After that you decide.

 

Here's how I do it on a table lift. First remove saddle bag's. Jack the rear end up and put a couple of 2x4's under the rear tire. Then lower just enough to let some weight off the rear shock's. Then remove the bottom 3/4 in. bolt's to both shock's. Get the 36 m.m. wrench from your tool bag, or invest in the flat ratcheting 36 m.m. wrench, remove c clip, and then remove 36 m.m. nut. Now lower the bike so that the rear tire goes up into the fender. Keep lowering until the axle clear's the lower bag support. Once you clear the support you can slide the axle right off with plenty of clarence. Just keep in mind to hold the rear caliper so that it doesn't mark up your wheel. This method work's great for me.

 

I for got to mention, you can leave the muffler's on with this method. If you don't have a 36 m.m. wrench, then you will have to remove the right muffler and use a socket.

 

A couple of you may have hit on something. When I bought the bike, I had them install an aftermarket lowering kit on the rear. That could explain why I have issues and you don't.

However, when I was trying the shock-bolt-removal-trick to avoid removing the slip-ons, I didn't notice that the swingarm moved significantly up/down with the shock disconnected. I raised/lowered the bike relative to the wheel, and I raised/lowered the wheel relative to the bike. Afterall, I was trying to avoid work, so I had motivation!

What I don't know is if it moved "enough" to allow the axle to slide out, because I wasn't that far along in the process yet. If so, that means I have to add a step to remove my shock bolts when I remove my tire? Would adding air to the shock lower the swingarm? I only need to go about 1/4".

 

You would need to raise the swingarm/tire into the fender with the shock bolt's removed. That will give you the clearence.

 

The swing arm does move up and down a good amount when the shock bolt(s) are removed. Adding air to the shocks will do nothing. By reading these posts, I'm going to order the Kastar Hand Tools 9636 - Rear Axle 36mm Nut Ratchet Wrench and not have to worry about removing my exhaust.

 

You sure your axle nut is a 33mm mines a 36mm.

 

To finish removing the tire, once you slide the axle out, reinstall one of the shock bolt's this will hold the swingarm up. Then push tire forward so that you can get the belt off. You might have to remove one of the lower belt gaurd fasteners to move it over to get clearence for the belt. Then you raise the bike up enough to slide the tire out.

 

The most important part of the job is getting the torque right on the axle nut. You can't do it right without a torque wrench, and not one from harbor freight. They are unreliable and go out of spec without warning. Harbor freight is the biggest problem with Harley fasteners. Stay away from harbor freight torx and allen socket bits.

 

1 7/16" will also do the trick as it is almost a perfect 36mm FYI
Sounds like the lowered bike is causing the extra condition.
I have never had this problem either with my 08 UC but know exactly how you feel about changing that tire for the first time! After you get the hang of it things will go much smoother then... I can do both tires on/off the bike in less than 40 minutes including the balance..
Some pointers
1. A warm tire is an easy tire to mount, keep it indoors until your ready for it preferably let it sit in the sun just prior to mounting.
2. I recommend using a tire paste to get that first bead of the tire on the rim. NoMar is the brand I use looks like vaseline just smear it around the valley of the rim lightly and on the outside edge of the tire that's going on first and life will get much easier...
3. The most important tip I can give both for removal and installation of your tire using a mount/demount bar is to make darn sure the tire is setting in the valley of the rim! I promise this will make the difference in a one man operation vs a call the marines I think I'm going to need some help scenario. That recessed portion makes ALL the difference. When you mentioned that the demount tip was bending I knew from experience exactly what was happening...