Hunter's are sweet! Hunter's and Catalina's. If I had the cash to be in a H or C in a 32', that may be where I would be now. I was forced to be resourceful, and look for what was available.
That's how I got the Hunter. I also looked at what was available - on a decent trailer. The trailer turned out to be the hard part, lots of boats around here in Maine. Lots of rust here as well, roads are salted, salt water, salt air.
Now that I have the Hunter I'm quite addicted to it. Of course, if it doesn't sail well out it goes. Meanwhile, I finished the Port side bunk and slept in there on the last few hot nights, cools faster than the house. I finished a small foot pump sink and stove so I can make coffee in there in the morning. I set up two solar panels and a single battery (should really have another) and have a tiny freezer so I can make ice cubes with solar power - the greatest achievement of modern technology - solar ice cubes for my drink on a hot summer day!
In "This Old Boat" Don Casey has a short discussion about changing rigging to a cutter set up. Seemed a lot more complex than I would have expected. Good book, I got mine for like $9 including shipping from Amazon. I expected a beat up paperback, but received a new looking hardcover.
I've found that raking my main (only) mast forward or back has a large effect on the helm. In my boat, I raked it back since I'd heard that was good for sail shape, but got terrible weather helm. I then raked it forward and got a nicely balanced helm, just a touch of weather helm and lots better sailing. Dragging that rudder through the water with weather helm slows you down.
Adding sail forward could give you lee helm, not good. I leave that stuff to the naval architects. That new pulpit and rigging sounds like it could double the cost of your boat. Pricey stuff! I consider you bold just for thinking of doing it.