It does require some finesse with the sheets
, and in light air it can still be a problem. Here's what we do:
Use the smallest knots you can to secure the sheets to the clew. We use a "luggage tag" or "cow hitch" at the middle of a double-length line. This is less likely to snag on the inner stay than a more bulky knot
If you are sailing with the staysail unfurled, don't tack the staysail until you get the headsail across. The staysail catches the headsail and guides it through the slot.
In light air, we have someone ready to go forward and pull the headsail through the slot. I usually try brute force on the sheet, but sometimes that doesn't do the job.
I've considered a "tricing line", which is tied to the headsail clew, led through a small block at the tack, then run aft to the cockpit
. You pull on the tricing line to bring the headsail clew forward during tacking. I've not actually tried this, because it is just one more line to snag on something, and we don't usually have that much trouble tacking anyway.
The classical way is to have a removable inner stay that you can secure aft, but I have a staysail furler
which makes it difficult to do this.