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I built a round deck, two tiers, two circles, 37 post holes. The hardest part is the cap on the railing... I am still working on it, I started by angling it from straight pieces, and that looked stupid so when the weather breaks I am going to borrow a friends swimming pool and soak some wood so I can bend it, I have never tried this before. In process modifications suck, my wife wanted to use a cap style railing after I started so that people could sit drinks on it.
 
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Finishing my basement.... 5 rooms and one bathroom. Took me a long time becuase I did it by myself with little help. I finally got going really good on it and then we had a sump pump failure during a bad storm and the basement flooded. I ended up having to redo alot of what I had done. That was my first major project and I learned alot by doing it but we moved 6 months after I finished so I never really got to enjoy it :(
 
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My dad single handedly (well with the help of my brother and I) remodeled their lake house. He build all new walls upstairs and downstairs, ran electric, ran the water and plumbing, put new wood over the old floor, laid down tile, put in a bay window, put in 3 patio doors, built a new 2 story deck, and put new 6x6 poles on the boat dock. The only stuff he didn't do was the heating and cooling system and the drywall.

The hardest thing I had to do was help pound the 10 poles into the lake to put the boat dock on. My hands blistered after the first one. We had to pound those things at least 3 feet into the lake bed. That week sucked.
 
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hardest thing, driving posts granted i have an old 25lbs rail road hammer, still abtich though.

the most skilled thing far and away operating a scythe. its impossible and if you do it with an old tiimer who can do it your ass sweats a ton to do a little and he looks like hes barely working and does a ton. a very skill thing, the movements have to be just right.
 
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Doing tile takes a lot of skill, and is a major amount of work. Personally, painting bores the crap out of me, and I can't stand heights, so no roofing for me.

Any job where you have to start with a room or floor that isn't straight just sucks also.
 
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I wanted my own room, and in 8th grade, my father said I could have one in the basement if I built it myself, as much as possible. He had me work on everything from planning, measuring everything, cutting 2x4s as long as Mom wasn't around, putting up the frame, setting up wiring, hanging drywall, sanding, sanding, sanding, more sanding, painting, putting down carpet... pretty much everything. Seemed like it took forever, but boy, was it nice to have my own space - really my own - afterward.
 
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