As to attaching the reefing lines directly to the cringles in your main's clew. Go over to Sailing Anarchy
Forums, & do a search on reefling line locks (&, or similar searches).
Some guys have setup their boats so that for all intents & purposes, they have
Halyard Locks on their reefing lines. And there's but one line & lock, connected to each reef point per clew.
It would seem that those that have them, seem to love them.
Making reefing easier 101; "the Beta Test" 
1) Attach an Antal (or other) low friction ring to your reef cringles with short Spectra (Dyneema) strops, or lashings. Both Tack, & Clew.
2) Make semi-disposable pendant "ends" (strops) for your reefing lines, where they take the most wear; out of
Dyneema. And splice loops into both ends of these.
3) Splice loops into the ends of the working
parts of your reefing lines. Being sure to
add a bit of extra anti-chafe sleeve, to the loop in the working part of your reefing line.
--> The purpose built stuff, not just standard line cover.
4) Thread the end of one loop through the other, linking them together.
5) Secure the Spectra pendant/strop to your boom in the usual place. Via either; a commercially made "shackle", a soft shackle, or a Spectra lashing.
So now, you have super low friction, long lasting, easily replaceable reefing lines (disposable strops, rather).
And done right, with regard to their length, you'll have zero issues with them sticking (or getting near) your in boom reefing sheaves. Plus, yeah, the effort required to haul in that last, super sticky bit of a reef will drop by a Lot.
NOTE: And this is an educated guess (meaning I haven't tested it on an
ocean crossing yet). But if you make long strops, & also use
Dyneema cored reefing lines anyway. You can link the strops together with the working
parts of your reefing lines while at the
dock. And then feed the joint of the two lines through your boom's sheave(s) while the boat's stationary. So that the joined section resides inside of the boom.
Plus, if your reefing lines are Dyneema cored anyway, you might just leave the cover off in the vicinity of the splice. Thus making for a svelte line joint, where the two are connected.
And some such connections feed pretty seamlessly over sheaves. Depending on the bulk of the lines, & the width of the sheaves.
Can't hurt to try, at least for your 1st reef. As if something chafes through where the lines join, you can go to reef #2 until you have a chance to sort it out.
It's not as if lines in booms are tough to thread, so have at it!
PS: If you do leave off the cover on the end of your reefing line(s) proper, remember to do a structural taper & bury with it. In addition to lock stitching it into place.