Last place does suck, especially when we were expected to compete those seasons.
However, going 30+ years with no rings sucked more. I remember saying I'd take 10 last place finishes for just one ring. After the first one, I didn't feel that way anymore.
Yeah, the seasons were exciting coming so close year after year, but those winters were long and painful listening to yankee fans saying "Ring scoreboard chump!"
There was also one pretty bad stretch back when the division was 7 teams. We finished 5th, 5th, 3rd, 6th, 4th and 5th in a 5 year stretch from 1980 to 1985. We followed that last 5th place season with a 7th game loss to the Mets in '86. To me, that loss hurt more than the previous 5 years of futility.
Funny, we went 78-84 in 1987 then won the division again in 1988.
Later, we finished 7th out of 7, then 5th and 4th from '92-'94 and again followed that with a 1st place finish.
The 8 straight second place finishes from '98 to '05 were exciting, but that ring in '04 was so incredible, it washed away years and years of pain and frustration.
I'm not sure I'd call 2006, 2010 and 2011 all that exciting, but they surely were more fun than finishing in last place. Finishing 5th out 5 in 3 of 4 years stung badly, but that 2013 win after what happened in Boston that year really did wash away all the 3 years of pain for me. That was special.