Coolant disappearing, head gaskets?

[6.7 Powerstroker]

I checked my coolant level again today and noticed it was a little low so I climbed under the truck and saw this little trickle coming down the front passengers side frame from this coolant hose connection. Looks like an o ring will need replacing.

I also noticed a nice sized oil spot that looks to be coming from my upper oil pan gasket.

I had this repaired about 3 years ago and the dealer charged me right at $1,200 I think to just change the upper oil pan gasket. Is there anyway to change the gasket with out dropping the transmission? Like unbolt it and lower it then slide the old one out and a new one in then rebolt it or no? I'm not so sure I want to remove the transmission myself so if not I'll have to take it in to the dealer. I thought about just loosening the bolts around the leak a bit then retightening them to see if that helps.

 

[6.0 Tech]

No. There are 3 small gaskets, rest is silicone. The trans bell housing bolts to the upper oil pan, so it really all needs to come out and get done right. ****ty it leaking agaun, they mighve smeared just a c hairs worth, and it started recently where it isnt as thkck as the rest.