Mike, while I'm highly inexperienced compared to your resume, I find reefing difficult for a few different reasons on my H34 and will be watching what you do with yours for tips and future possibilities. My normal process is topping lift on, mainsheet and vang slacked, lower halyard, lose 1-3 slides out of the mast gate so the luff reefing ring can reach, put luff ring on hook, raise/tighten halyard, then pull in the clew ring reefing line, and finally adjust outhaul and loosen topping lift, retrim mainsheet and vang. Pretty standard on most boats I think.
Where I run into trouble is the luff ring always wants to come undone especially in gustier conditions as my wife battles to keep us head to wind (we're still slow at the process), the other is the clew ring doesn't really seem to snug down to the boom very well unless I loosen the main halyard a second time, pull the clew ring in
really tight, then reraise the halyard a second time. The last time we did this, I didn't catch that the luff ring slipped out again and I put a hole in the luff of my main with the reefing horn!!!
My own mistake but its how we learn.
I have been thinking of going to double line reefing by using turning blocks at the mast base, using existing luff rings and running luff reefing lines tied off at the boom like you would the clew side lines. Run from boom, through rings, down to turning blocks, through deck organizers and to additional clutches on starboard side. I'd then run the clew side reefing lines similar but down to port through additional clutches. This would eliminate my issues with the luff ring, and give me better control to really get the reef close down to the boom rather than 12" off of it. My main hanging point is what to do about the luff cars that I normally remove and subsequently put back when shaking out the reef.