Hey @Logan, @DeusQain. Inspired by this post, I was just curious if you've thought about having another HighLANder-like event.
I'd like to submit Wizard Island, located within the caldera of Crater Lake in southern Oregon as an option. Its ~7,000 ft high and would tick both the land and sea (lake) boxes and could be pretty awesome.
I've never visited myself, but according to the wiki, there is boat access to the island during summer months. Potentially, if the park folks let you, you could catch a ride over and then climb to the top. I figured it could be a good idea since you are located in Portland now. Perhaps you could coax Paul and Kyle to join in as well.