Healthcare is definitely the toughest budget item to predict.
That and college expenses.
I’ve been lurking a lot on http://www.early-retirement.org/forums/ – lots of good advice over there… but it seems like many of the regulars are retired military, so they have pension and medical insurance covered.
They also have a calculator that let’s you “what-if” different scenarios, and runs Monte Carlo simulations to see if you’ll run out of money.
For my dreams of retirement I know it works better for me to have the mortgage paid off. We’re also putting money into the house now so we won’t have to later… in anticipation.