So my 2011 Wide Glide was shifting hard into first so I went to adjust the clutch and saw that there was very little oil inside the primary. I filled the primary case again with fresh oil. Should I be worried? I rode is about 1500 miles since I changed all the fluids.

 

I sure would be looking for some oil residue on the bottom side of the primary case!!

 

The ring gear dips way down in the primary. It would sling oil with only half the required amount. Are you sure it was really low. the owner manual sucks on what it shows. It should only be to the edge of the diaphragm spring. It's so hard to really see the proper level, I have a little piece of bent wire to check it. Next time you start it, try pulling in the clutch and push back of the seat pushing the bike back about a foot. It helps to break the dive and driven clutch plates from the oil film that sticks them. It will ease the clunk a lot. If while you do it, and tap the throttle a couple times and one the second as it drops back to idle, hit the shift and it will not clunk at all (most of the time)

 

After that amount of riding, check your primary level again. If it's gone significantly lower, that's not normal. Several places it could be going.

 

If you lost the amount of oil you think you did, there would be a oily mess on your bike.

 

Drain the primary, put in the 1 qt. that it calls for and check it again. You can barely see the oil level when the proper amount is in the primary.

 

When you drained the oil did you look at the drain plug ? It has a magnet in the middle. It is usual for it to collect a black dust but if it has collected metal chips or flakes that is the time to be concerned.

 

Did you check the oil on the side stand or bike straight up and down. As stated right to bottom of diaphragm spring. Any drops where bike normally sits? Check the trans fluid level and when was it last changed? That would be my concern unless the primary tensioner went bad.

 

If you're losing that much oil, and it's not leaking, your crank seal is shot and the bike is sucking primary oil into the crank case. Yes, I know, it sounds like bull ****, because motor pressure should be greater than primary pressure, and if the crank seal was shot, it would be the other way around, but I had this very exact same thing happen to my bike. The PO put the crank seal in backwards. The only reason I noticed this is when I checked my oil on a fuel stop... which I do EVERYTIME I stop for gas, and the damn oil was full of red ATF and right up to the filler neck where the dip stick goes in. Of course mine is an evo and yours is a TC, but... not very different from each other when it comes to the primary. My recommendation is to pop that dip stick and check it.

 

Check your oil level.
My manual says 26oz... on mine. 05 super glide.
If doing by sight make sure it is level not on jiffy stand. The fluid should touch the bottom of the clutch basket. Check you service manual for your bike.