bpw,
Not many people are going for a wooden unstayed mast these days. A better option (I'll try to avoid saying best, as it upsets some folks!) is a spun-tapered alloy pole, widely available these days, as they are used for streetlighting and flagpoles. Look at, for example, http://www.crescent-stonco.com/uploads/library/Spec/RTA_30_50_PC.pdf
to get an idea of prices, sizes and weights. My mast is 12 metres long, 220mm dia at deck level, 100mm dia at the head, with 5mm wall thickness. I can't recall what it weighs, but the important thing is that the CG of such an unstayed, tapered pole is much lower than the usual parallel section, stayed rig. If I'm moored in a line of similar-sized boats, all the rest with bermudan rig, then it's easy to spot me - I'm the one with the very much lower rig!
The pragmatic option is to buy a parallel alloy tube from a stockholder, as long as you can get it, and then to build a tapered, staved wooden topmast. I recently did a calculation for the owner of a 26ft boat, who wanted to replace his solid wooden mast, and the weight of a hybrid mast was about 64kg, against 120kg for the solid wooden mast.
For a 33ft cruiser/racer, I wouldn't consider going to a two-masted rig. I don't see any advantages in manouvrability, and as you say, all the costs and weights are going to increase. I have a single masted rig, 630 sq ft on my 35ft, 8 ton displacement boat. That's a bit of a handful, but up to about 500 sq ft total area, it's best to stay with one mast, one sail.
You'll look in vain for hard numbers on windward performance for JR. We've been trying for many years to get boats to sail together, some with the many and various forms of JR, some with the many and various varieties of bermudan rig, and it's a remarkably hard thing to achieve. Boat-against-boat trials are the only genuine way to compare rigs; one boat recording it's VMG in one particular set of conditions doesn't help very much.
So if I did my math right your spar should be about 172 lbs for the bare tube, not bad. I will need to check if something similar would be strong enough for our new boat. Our righting moments my be quite a bit higher than your boat.
Two masts (or a headsail)would be needed for us, I would not feel comfortable sailing into a tight spot without the ability to back a jib or foresail to help control the bow. And I would be looking for 700 plus square feet of sail.
It is good talking to someone with a good bit of first hand experience with the junk since I am quite interested in it. Thanks for putting up with getting poked and prodded.
I think my ideal would be something similar to what Eric Sponberg did for Capernicus, a freestanding single masted fractional rig. Most of the advantages of a freestanding rig, while retaining a headsail for manuverbility. Maybe carry running backs to allow some control of mast bend and headstay tension. Requires a tall mast though, so the weight might be tough to keep under control without carbon. Maybe with a full batten main it would be OK since I could shorten the mast and still retain sail area.
Can capernicus set a spinnaker?