I have a suburban with a SBC 350 that is leaking out the driver side valve cover, but it was manageable until I made more money to repair. Now the passenger side is leaking right above where the plug wires meet plugs, leaking so bad I have oil down the side of my truck! It also won't got past 1st gear, which is a new development that came with the massive leak on the passenger side. I haven't began to replace anything until I know where to start, but I need some SOLID opinions to save this truck. My oil is going everywhere, my wheelwell is wet, drive shafts, tranny, hell even my side steps

 

Welcome to the forum,
Replace the valve cover gaskets and that should address the leak. Its been my experience oil leaks are caused by poor maintenance of letting the oil get too old or too thin from excess fuel being dumped.

 

Would that help address the issue of not getting out of first gear? I have an automatic and right now I can hit 5k rpm and it won't shift even when i feather the gas(which used to work)

 

Those items are not related. Something that old ,the transmission Is likely needing a rebuild. It's been done twice on my '94 with the most recent just last year.