A few comments from my experience/perspective as a racing sailor FWIW...
First, I don't think I would rely on AWA as a particularly accurate indicator of pointing ability unless you have very high confidence in your instruments and calibrations. Try as I might, my AWA varies tack to tack with new Raymarine i60s. I prefer to look at my overall GPS tacking angles which account for leeway angle but also factor in current. I find that my actual tacking angle with full main and fully powered with 150% genoa (talking 15+ knots AWS) is over 90 degrees. If you assume something like 5 deg leeway each tack, you should see under 90 degrees tacking angle on your compass. The boat is moving along nicely though at well over 6 knots and I'd venture a guess that I'm making better VMG than the OP. I keep my bottom clean, have a feathering prop, and my CB is faired quite nicely. I think these things help a lot.
Sail shape and driving ability really has a lot to do with all this. T37 k/cb polars are out there and if they are accurate you should be able to sail close to upwind targets so long as your boat is fairly optimized and trimmed properly.
My impression having sailed the T37 a few thousand miles this year (much of it upwind, including NY to Chesapeake Bay last month in 20-30 knots) is that the boat likes to sail powered upwind with the rail near the water. It likes some helm which keeps the boat tracking properly. While reducing sail and moving the CE of the sailplan forward makes for a more balanced helm, it may also hinder how the boat tracks and you may end up oversteering some if not really working hard to stay focused. More balanced is definitely better if you are sailing with an autohelm and you are worried about power consuption.
I do think that taking that first reef in the main before furling is the way to go if you are overpowered with a smaller headsail up (I have a new main with lots of roach and a new 115%). This allows you to put some leech tension on for point w/o getting overpowered. I also think that if you have a furler like the Harken or Selden that allows you that "free first turn" to take out some of the depth in the jib without really taking out area you will see improved sail shape when the breeze is on.
So, my experience is that the T37 points OK but ultimately it is limited by several factors not all of which we can control. I would expect the deep keel version to point significantly better because of a more efficient keel shape as well as a lower VCG.
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