Re: Back in far enough!
These stories are great! Now it is time for me to add my own.
We just bought our first boat last month:
http://www.seaworx.com/files/boat/chaparral183ss
We took it out the day we bought it, and pretty much experienced every mistake that could be made. =o)
I backed the boat down the ramp just fine, and it was starting to float. I stood on the tongue of the trailer, my feet now wet, and tried to give the boat a little push to get it going off the trailer with the slack I had given the winch strap. Well, needless to say, my feet slipped right out from under me, and I ended up laying on my back on the tongue of the trailer. =o)
After I launched the boat my wife drove the truck/trailer back up a pretty long and steep hill the parking area. About this time I realized that the new life jackets were still in the back of the truck. So I was going to call her and tell her to bring them when she walks back down, but she had already put her cell phone on the boat. So when she got back down to the ramp, she wasn't happy at all to have to walk all the way back up to get them.
Finally we were able to cruise around the lake for a while, when about an hour later I'm like "Oh crap! I never put the plug in." So we go back to the ramp area, and I jump out and put the plug in, but at this point we were ready to call it a day and take the boat home. It took 2 or 3 tries to get the boat straight on the trailer, and then we pull up the long hill. My wife says, "What is that noise?". It was "Oh crap!" again. With all of the other events, I had not remembered to raise the lower unit and the road had ground off about 1/2" of the skeg.

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Needless to say I learned a lot that day. The funny thing is though, that I have had to jump in the water a couple more times to put the plug in (good thing it has an automatic bilge pump).
On the way home one of the trailer tires had a blow out, and a friend brought a couple tires from his boat trailer to get us home.
Some of the lessons learned:
1. When you buy a boat (used at least) don't take it out on the water right away. Take it home first and check everything out (trailer tires too).
2. Remember the plug!
3. If you are new to boating, make a checklist for:
a. Things to do before leaving the house.
b. Things to do before/during launce.
c. Things to do during/after re-trailering.
d. Things to do when you get back home.
3. Make sure your wet feet have traction!
4. Remember the plug!
Stay safe, and keep sharing and laughing,
Strider