All Line = Good!
Our '88 Kenyon spar has sheaves that do accomodate 5/16" line easily, but 3/8" is tight -- too much friction, we decided. I did try both line sizes on a couple of halyards when converting from the original wire-to-rope-splice stuff.
The good news is that the low-to-no-stretch New England Rope T-900 in the 5/16" size will hold in our existing clutch stoppers on the housetop.
What with the strength rating of this size line being about 7000#, they are about as strong as the fixed rigging wire on the boat, so strength, per se, is not a concern.
If your masthead sheaves are too narrow, go with a 1/4" halyard with an extra cover layer on the portion you handle when it is hoisted and you need enough diameter for good handling and holding in your particular clutches.
Opinionated Sidebar: if your boat has old early-technology "rope eaters" for stoppers/clutches, change 'em out for the much-improved Lewmar "falling rings" design. Yup, they really are (!) that much better.
Note B: when you make this change, remove those masthead sheaves and machine all the burrs out of them. After years of deteriorating wire strands abraiding the metal, they will probably be rough, and potentially chafe on your new line. Mine were aluminum, and needed this.
They might need new bushings, if they have 'em.
Note C: if you feeling especially flu$h, change out the main halyard sheave up there for a ball bearing Harken sheave and reduce the inherent friction drag in that 180 degree line turn... This should make the main a little easier to hoist.
Best,
Loren
1988 Kenyon spar / Olson 34 tall rig