I was figuring on the new headgasket, I just wasn't sure if it was an issue where the spots where the metal meets has warped over time because of heat or something. I think I may even have oil leaking where the cylinder meets the case. I'm not sure, kind of messy, I'm gonna dig into it more if it stays dry out today.
Thanks for the advice Dave. I don't have a torque bar right now, so I don't wanna strip anything out, but I do have a sears credit card, hah!