Skeptimistic: Being skeptically optimistic.
“My wife and I just toured an abandoned military base in upstate New York, and I’m skeptimistic that it might just be the perfect spot to raise our hideous children.”
“I was skeptimistic about your idea to fill a child’s swimming pool with live shrimp and film yourself crying in it, and while I’m not sure it will be great for your career, you did make us both a lot of money. So thanks, Doug, I really mean it. Things were rough there for awhile, I almost lost the house… my family… Everything… Shit, I’m tearing up here. Just thanks for including me in this, man.”
Part of me suspects that someone has put these two words together, but I did a google search and didn’t see anything, so it works for my list.