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I have a similar generation Montauk to yours, and I agree with the others on engine mounting. These boats have a shallow engine well, and the standard 8" vertical separation between top and bottom bolt sets can not be accommodated. This is what evidently confused your installer.
As mentioned, instead use the 6-1/2" vertical separation, accomplished by putting the bottom bolts in the top holes, and top bolts in the THIRD set of holes from top (two empty holes above the bolt). This will allow the bottom bolts to come through the transom and receive washers and nuts. These bottom bolts should go in from the outside. This will effectively raise the engine 1-1/2" instead of Whaler's recommended 3/4". Whaler never recommended the engine be all the way down on the transom. Performance will be improved and you should not get any prop slippage, even with an aluminum prop.
See linked photo of mine. The bottom bolts don't show in the picture but they are there.
For $25, the stiffener bar across the top bolts is a good idea with a heavy engine.
Phil is right about the bilge pump hole in the splashwell. That definitely should be filled in. The discharge hose can be bundled up with the engine rigging to dump over the transom. If you look at my photo, you can see the 90 degree clear "L" fitting just above the fuel bulb.
Black hose makes it disappear in the rigging bundle.
Thanks for the responses. Currently the motor is located in the 2nd hole from the top of the motor bracket. The only way I can have a bolt in both the top and bottom and lower blind hole is to mount all the way up in the bottom hole on the motor. That would be raising it 2.25". I was very squeamish about using a lag bolt on the bottom. The current 2.25" separation had good transom wood, and I felt good about mounting the second set of bolts here.Wish I had the sketch showing the bent/cut washers next to the well curve. That would have given me more thought. I am good with moving the motor all the way up. How will this affect performance? Performed break in on Saturday. 38 mph @ 5600 RPM's with the aluminum prop. We searched hard for vibration. Couldn't find any.
The hole in the well that carries the bilge hose was cut in by the dealer that sold my father the boat new. It had a plastic sleeve that cracked and I removed it. I was informed by someone on whalercentral this wasn't a common way to route the bilge hose. Nonetheless, it was done. I purchased a 3" hard plastic cup holder from West Marine, cutting the bottom out to fit. Used some silicone caulk. Came out really good and is all sealed up.
Also, earlier someone had posted that the motor was sitting on the transom. Since then their post has been edited. FYI - There is more than an inch from the transom to the bottom of the bracket.
Hampton, no one is telling you to use lag bolts or to use the blind holes. If you read the article posted earlier carefully, you'll see the best option is to drill the green holes and mount the motor high, which is better in your situation anyway.
Yours is not the first motor I have seen mounted that way, but I continue to believe that it's simply unsafe to have the bolts that close together, concentrating all the stress on a small area of the transom.
With the motor mounted higher, you'll immediately notice lighter and more responsive steering, and increased effect from motor trim changes.