Before doing too much, I'd suggest talking to 5 or 10 other 37 owners. For instance, with the long boom, even if it is "too long", your new sail can be cut shorther on the foot. i know you just bought the boat, but you will be advantaged by not making major decisions till you've sailed her a bit. Talk to some other owners and explain the deficiency of the mast--seems like it may have already been shortened--ideally, you'd want to know what the mast height should be. Frankly, I disagree with getting the hollow cut main, but lots of folks with similar boats do like them. My preference is always towards higher performance because one can always shorten sail, but in light airs, I don't like to motor
if I can sail. Many years cruising behind this point of view--about 27.