Answers to the questions first:

1. I drilled a 1 1/2" hole near the top of the lazarette bulkhead. My recollection is that I sealed the hole with a sulfite sealing compound. I would today probably use 4200. So, there was no fitting used. The flexible hose for the electric pump just continued vertically downward from the top of the bulkhead to the bottom fitting located above the water just to starboard of the aft end of the motor well (so I didn't have the bad visuals of a large fitting sticking out the transom). In the case of the Whale, it too is a continuous flexible hose going through a 1 1/2" hole with sulfite or something sealing it in. The hose bends and points downward.

2. Yes I did cut a hole in the side of the bench (cutting the glass always hurts - what happens if?). The Whale has a plastic plate as a cover with a rubber-like gasket. I don't recall using any sealer and have had no problems with leakage. I do recall that I had the same question you raised and perhaps had to purchase separately the front plate and gasket for a vertical mount. The plate is very nice, with a flap that covers the whole thing when not in use, and flips up exposing the pump handle connector (The opening is still sealed, however).

3. The pump is hung from the cockpit wall and is very rigid. There is no shelf. Keep in mind that the mounting is aft of the cockpit scupper, and just under the horizontal bench, so there is lot to hold the vertical wall rigid. All screws are through the vertical wall. The 4 degree scupper drain on the afte end and inside the opening offers protection for the pump body.

Space: The flexible hoses after they pass through the lazarette bulkhead are cable clamped to the bulkhead so they don't take lazarette space. The electric pump hose goes vertically down into the well, then bends horizontally to where it bends to meet the previously mentioned through hull. All hosing is under the motor well platform.

One last thing. I mentioned using flexible marine quality (not Ace Hardware) coil type hose rather than the more rigid Shield's hose - that really should be used. I could not figure out a way to do with this with the more rigid hose. I have had no problem with flexible stuff, but recognize that the hose walls are not as heavy. Since the hosing is not exposed to sunlight, I con't imagine having a problem but conceivably there is a weakness there. That is one reason why I have two independent pump exit lines - in case one starts leaking.