Looks like you have a very sweet boat and got very lucky with the rig. I have been cruising with a junk rig for 8 years now and would never, never change things. Unless I wanted to win races around the bouys. (we have raced her and for sure the upwind leg in flat water
will kill you). However, that truly makes no matter if you are simply out there to sail for the day or cruise
The headsail will for sure help windward performance, if that is of great concern to you. I would simply measure what size jib
will fit to the rig you have in place, and then find something used to give it a try.
My boat, Willow is a junk rigged schooner and I do at times wish I has a jib
to fly up forward, but only very rarely. We have made some very difficult windward passages with this rig and have done just fine.j
Well, I have no real words of wisdom, but do have this to say.
"A junk rig on the horizon always improves the view."
Perhaps something I have written on my website will help. Log of s/v Willow
It is the easiest rig to sail and low stress with it.
Greg from Hilo Hawaii