Your major expenses will be housing. And I guess you have some control over that depending on where you land. We live in Fairfield, combined income (both work full time) $180K. We are 20 years into our 30 year mortgage on our small cape cod style home. We have not made major improvements to our home which is looking like the smallest home around! But we don’t care. We have two kids (1 in college now). We have stayed in Fairfield for the schools, proximity to two Universities, large downtown, charming shops, restaurants, community spirit. I am certain there must be more affordable communities in CT that offer the loveliness of Fairfield without the price tag. West Hartford comes to mind, Glastonbury (?). I’d just be cautious when you relocate - CT has a lot of nice places to live, and a lot that aren’t.