Cool thread.
I have an extremely long list, but the two at the top are:
-Paying landscapers to re-do our back yard
-Replacing all (most?) of the boards on our deck
Our lot is long and skinny, dividing pretty much into thirds. The front third has our front yard and house. Middle third is pool on one side, and long skinny yard on the other. Way back yard is overgrown trees/weeds. We moved in four years ago and intended on doing the way back ourselves. My FIL came in and cut down a bunch of small trees, and we hacked away at the rest. When we got that all gone, we could see that it was 99% weeds, and 1% grass. Too big of a job for us at the time. Four years later it is in worse shape, so we had someone come in and give us a bid on removing all the brush/weeds, getting rid of all the trash (previous owners had a fire pit made of broken up concrete, and left the old pool water filter, as well as extra shingles and other trash from the poo house), leveling the ground, adding dirt, and sodding the whole thing. $6 grand was the bid. no idea if that is a good price, but I know it would be a every weekend of the summer, 10 hour days, of doing that myself and that doesn't interest me. I hate to pay for stuff like that but if I want it done before all my kids go to college, I see no other choice.
The deck is in bad shape. A lot of the boards are soft and need replacing. It needs to be repainted as well. That I can handle myself.