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Kevin,

I don't know what you mean when you are describing a 45 degree angle. The drain tubes in Whalers more often than not do NOT come out of the hull perpendicular to it, but they rarely are angled more than 5 degrees or so from perpendicular. The most severe angle I have ever measured was 13 degrees in the bow sump drain tube in a 22.

Yes, I would pre-flare one side on the tube at an angle top match the hull, then slide the tube through (with an O-ring in place under the flare) and then scribe and cut the other end so it ends up 5/16" beyond the hull.

You then anneal that end, butter up both ends with 5200 and pop the other O-ring on and then flare the other end. Clean up the mess and you're good to go.