First, advice:
Go seal clubber for your first HCO (if you haven't already), the shiny there will be most helpful. Your first skill pretty much has to be the L15 skill to be able to smash and create wads, which are a godsend in HCO.
The first run is probably going to suck. A lot. I would recommend saving adventures for stat days to make sure that you get everything you can.
HC is a much different animal than SC because it is just you against the kingdom. High level and awesome weapons do not immediately abound, so check the shop for a few things if you are struggling to do damage.
Hair spray is your friend. Use your friend.
As for BM. I went through the BM loop and it was not too terribly bad for the muscle classes or the moxie classes, but the myst classes will make you cry. They're miserable. I don't even really know how to adequately express how awful those runs are. That is why I took a long, long break there.
Fortunately, you're going through on a newbie character anyway and you've not had a whole lot of ascending experience on any character (while I waited until about ascension number 40 to start BM, which was bad. I loved all my shiny skills), so it might not be too bad for you.
As for the clan leadership, you weren't even the "leader" when I got it. It went from Trerro to me. So,
.
Tyred