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You can indeed get good ratcheting crimpers for $35-40 and easily for $50. At the same time you want proper crimps to use with them, look for Ancor in the chandlery or something similar at the big box store. You'll pay between 10-50c per crimp in small packs. But the ones that are "500 for $5" should be avoided.

It isn't unusual to have the pump and float screwed to a piece of wood, and then have the wood secured to the hull. That usually gives you more options and fewer holes in the hull, i.e. you can epoxy the wood to the hull, and then still unscrew the pump when it fails--because they all do in a short time. Look for a way to get them further down in the bilge.

Solder will work, although if it gets wet at all there will be a galvanic problem and a failure. If you solder make sure the wires are tacked to the hull, so the soldered joints can't fail from vibration and flexing. And that you are using adhesive-lined heatshrink, which tends to be waterproof when applied cleanly. I'd suggest two layers of it, overlapped, to help that.
 

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"You mean the board should not be free floating in the bilge?"
Correct. Usually, the "board" will be oriented vertically, on the side of the pump and float if possible. So that the bottom of the pump is exposed and sitting in the bilge, and the board is then mounted to the side of the bilge.
Exactly what you do will just depend on the exact shape, the slope, etc. of your bilge. You may find a plastic or metal "L" stock or something else works better for you. Metal is likely to have galvanic problems or rust, so wood or plastic is better for this.

"The electric bilge pump is plumbed through manual pump, is that correct? "
If you mean the discharge hose? That should be separate in an ideal world. It should go all the way up to deck level, as a siphon break or with one installed there, and then come back down to whatever drain level. Again, you have to adjust that to match the reality of "I can't make a hole there" or "I can't get a hose through there".

"How do I join two different sized wires? " There are actually crimp connectors that are made for a different size on each side, i.e. 10/12 on one side and 14/16 on the other. But what some folks have been known to do, is simply double or triple up the skinny wire until it is now as thick as the thicker wire. And use whatever crimp fits that one size. If you've made a good solid crimp, there should be no problem with this.

Also, practice with your crimper. Take a wire, crimp it, and now pull on it with all your strength. If you can pull it out--something was wrong. If it stays in, you're ready for prime time.
 

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"Do i triple over the exposed wire portion of it before inserting to be crimped?"
Double or triple, as necessary. Or you can just cut a short bit of wire and stuff both of them (stripped, of course) into the crimp. That way there's no bulge where the wire has been doubled over.

"I am not sure of the details but think the wire to the pump come from right from battery without a switch. " Often a bilge pump is run directly to the battery so it can still work if the DC panel is turned off.

"I have seen Auto-off-On switches on other boats. Should I install one?" Again, a matter of personal preference. Whether it is one switch or two, and how you run the power through the pump and float, is all personal preference. The first time I tried to wire up one of those auto-off-on switches I just kept looking at the wiring diagram saying 'Huh?' because it wasn't the way you'd wire anything else, and on a hot humid day I'm not always there.

"The discharge hose from the electric bilge pump takes a serpentine route to a hand pump in the cockpit locker ..."
Well, sometimes installations are a compromise and sometimes they're just wrong. If you needed both pumps at once, and the electric one was discharging through the manual one...You'd still only have one pump really. Right? If both run separately, even if they share one discharge thru-hull, you still have two pumps working. And if something clogs the intake of the electric pump, you'd probably be happier if the manual pump was entirely separate too, right?
So it is a question of either doing it right, or deciding not to.

We had a similar problem of "there's no easy way to run a second hose" from the cockpit pump to the bilge. Compromised by coiling six feet of intake hose, with a brass strum box on the end, under the galley sink. If we needed the manual pump, we could always open the cabinet and pull the hose down into the bilge. Or, live with it under the sink and have a foot of water in the cabin. Either way beat nothing, and the floors were NOT coming up right then for that job.

Sometimes you flip a coin. Work until a certain point, and then it is time to go sailing.
 

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je, you never know. That pump could have been installed "wrong" because it was the only way that it fit. Or, the PO might have had a bum left arm and used his leg, or a crew kneeling and facing aft. You just never know what's "wrong" until you've tried to install it on the exact same boat, and a simple project turned into the usual three day long boat job.

As the joke goes: "And the madam said, ain't no way that's going in there."

Of course I also knew a top-name custom boatyard that managed to install two of the primary winches backwards, on a brand new yacht. Sometimes, it is plain wrong.
 
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