looks like oil?

My guess is your losing the output drive bearing and seal. by under the transmission do you mean all over the sump plate and if your getting oil on the wheel your drive shaft tube might be taking on oil. Easy check would be to drop the final drive and see if oil comes out of the tube or you can drop the sump pan and look in the rear left corner for metal bearing parts like cage pieces.
 
My guess is your losing the output drive bearing and seal. by under the transmission do you mean all over the sump plate and if your getting oil on the wheel your drive shaft tube might be taking on oil. Easy check would be to drop the final drive and see if oil comes out of the tube or you can drop the sump pan and look in the rear left corner for metal bearing parts like cage pieces.

What he said ^. Better sooner than later.
 
What he said ^. Better sooner than later.
After sleeping on it the only other things I could think of that will seep oil down the back of the engine would be the oil sending unit sensor, the cam cover gasket, and since yours is a 06 and has not been taken apart, it has the old style head gasket which might be seeping between the head and block in the back. Myself I am still betting on output drive bearings and seals. This could get pricey if your talking update kit because they have jumped to 1200 USD. If it were me I would take her apart and replace what is needed instead of the complete update kit. Not that the kit is not worth it.
 
After sleeping on it the only other things I could think of that will seep oil down the back of the engine would be the oil sending unit sensor, the cam cover gasket, and since yours is a 06 and has not been taken apart, it has the old style head gasket which might be seeping between the head and block in the back. Myself I am still betting on output drive bearings and seals. This could get pricey if your talking update kit because they have jumped to 1200 USD. If it were me I would take her apart and replace what is needed instead of the complete update kit. Not that the kit is not worth it.

Some pics of the leak would be helpful.
 
Some pics of the leak would be helpful.
Yes that would help with my gestimating :) also check crank angle sensor, Starter, and the rear cover gasket. I think these are doubtful but easy to check and well as oil plug sealing washers plus a good inspection of the sump pan. I have seen a few get cracked going on trailers and I suppose if your not careful you can crack the sump pan jacking the bike up. the only thing else I can think of is the gear position sensor but it is a O ring gasket on her.

Hey Fred I have been digging thru my parts organizing things and guess what came with the 07 in January ?

A new silver out put drive cover. Triumph of Indy must have ordered the wrong update kit when Todd Nelson owned it :)
 
Thanks guys!!!!!!!!!I'm going to load her up and take her to get examined by someone I trust more than me! lol I 'm hoping it's that seal to warp! Got a busy day today! I'll try and post a pic or two soon!
 
Maybe the same problem I had. No noise or roughness when driving but oil running down back of the rear drive cover and dripping on floor when parked up, also small amount on the rear tyre.It was hard to tell where it was coming from. Turned out to be the seal on the Final Drive unit. Oil was gettig sucked up the tube and coming out of the rubber boot at the rear of the Swing arm. An oil check on rear bevel drive is quick and easy.
 
I would check the final drive first even pull it as it is easy. Plus you can lubricate the splines and inspect everything there. If you can pull the rear wheel you can pull the final drive out.
 
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