Patrick,
I spent a lot of time, a fair bit of money, and put a few engineers on the problem for the Worrell. Here is what is known:
A) Yes, mast compression is a concern, however, it is truly a concern for wing-masts that are iffy. Basically that means the current Nacra mast section used on the F18 (Infusion on up), and the AHPC/Goodall section used on their F18. The Cirrus mast section is beefier, as is the section used on The Edge F18. Oh, said Nacra wing mast is being used on the new 20. My only issue with that boat. Its OK if you don't go sailing in waves (the west river doesn't have waves).
B) A simple tail is the answer for these boats, basically a dyneema strop from the original halyard attach point. I was trying to get fancy; avoiding the horn cleat, trying to avoid a 2:1 turning point on the masthead for weight aloft reasons, and retaining the ability to unreef under-way. I suspect the answer there is a second hook on the mast (side mount). Risks there too with loading/attachment, modifying masts etc. In the end, pull more downhaul and move on....if you need the reef, you'll need it all day.
B) When moving to more traditional masts, I don't think the compression issue is a problem. I say that as a Hobie Tiger rounded cape horn with reef points and a horn cleat. I believe your Wave mast is fine; that crack likely appeared due to water ingress/expansion, not sailing loads. Vlad's point about lowered sail area should also be noted. Any reef on a Hobie Wave is a big reduction in power, on a boat that is very underpowered to begin with. Despite what the sailing "instructor" at Sandals told me, the boat is only fun in 25kts with full hoist.
The real risk with the hobie wave are the attachments to the hulls, both beam and shroud anchors. They have pulled out, but this you know. Just keep an eye on them.
In summary, I wouldn't go buying H14/16 masts and modifying them for your wave, unless you just love spending money. The comptip plus associated mods JT has sorted you with are fine. I might invest in more downhaul purchase...and a luff patch.