Interesting thread - depending on the individual. I experienced a variety of 'feelings' toward spending over 20 yrs of ER. Hindsight says I was overly cheap/frugal early in ER being worried whether it would last and whether I could endure the ups and downs of my portfolio. As time in the market greatly improved my circumstances I was uncomfortably spending more as FireCalc , ORP, and the 4% rule indicated I was safe. But breaking my old perceived 'frugal' was at first painful.
Unplanned events - some well paid temp work early, Katrina, getting married and finally getting to the point mentally (you can't take it with you) has allowed my spending to loosen up as it were. The onset of RMD with the IRS taking their cut has affected my mental williness to spend more.
heh heh heh - so far health issues of significance have not surfaced - knock on wood.