Central Illinois - basically everything within 50-75 miles of I-74 across the state. Doesn’t get bitter cold, not overrun with MAGA asshats (among the reasons we left another Midwest state), cost of living isn’t terrible, and easy access to Chicago, St Louis, and beyond.
After you spend down your allotted PTO, yes.
Mildly surprised that someone in a position at that level wouldn’t have at minimum short term disability coverage, at least as an option. It’s hardly expensive.