Thanks everyone for all the info.
Ive had this bike for several years. I have a original factory manual for the bike and a clymer manual for that matter, from when my dad had Ironheads and a couple basket cases years ago when I was a kid. I'm not really a stranger to these bikes, this one is just doing a fantastic job of aggravating me. As for the wet sump issue, I know its not that big of a deal just more of a mess than any thing, Its a very slow seep, like I said more of a mess and annoyance than any thing.
Tomorrow evening I'll recheck the timing and push rod adjustment. The carb should be good as I pull and cleaned it this week before attempting to start the bike and the petcock is brand new, installed tonight.
Edit: No fuel was left in the tank or carb/fuel bowl over the winter.