Headsail anchor to bowsprit

[CaseyMcM]

Would you mind filling me in on some of the ways it could go wrong?

This is a code 0, about 100% jib equivalent, very flat cut (intended for reaching) with a sewn in HM luff line that it is furled onto with a continuous line furler. The yankee sheets will be tied out of the way when this is flying and this sail will be bagged on deck when the yankee is flying. The tack will be aft of the jibstay (ahead of the forestay w/staysail) and it will be hoisted with a spare jib halyard where the upper swivel will likely be 2 feet below the jib furler swivel. As you suggest, there isn't much room in front of the cranse iron and the furler would foul with the jib furler.
I bought the sail used from a gentleman who was using it in a similar way on an Ingrid 38, and here is a sister ship to mine doing something similar.

[Brion Toss]

Hi again,
There are lots of ways to rig light-air sails, and of course the easiest way is not always the best. One configuration involves tacking the sail aft of the jibstay, but hanging it from a spinnaker halyard crane. This would of course foul the jibstay, and I had feared that this is what you were considering.
Instead, you would have the halyard below the jibstay, which prevents that fouling, but only at the price of reducing sail area by 70sq. ft., or about 15%. On a light air sail, this is an unacceptable price.
There are other issues, like chafe on lifelines, the inability to fly Genoa and drifter together, optimal sail shape, etc. I have no doubt that the gentleman you reference gets good use out of his setup, but I very much doubt that his solution is optimal. And while we are at it, let's look at what he has done, starting with load calculations. He says that what he did is based on a "common-sense, educated-guess approach," and that he, "overbuilt the fitting to give us an added safety factor." And then he shows the formula he used, which is for sheet loads only, not for the load on that bowsprit fitting.
Nor am I impressed by the vulnerable-looking halyard crane he installed. And what's with the upside-down DVH on his Genoa furler?
My recommendation would be for you to get in touch with my hero, Carol Hasse. She is an extraordinary sailmaker, sailor, and human being, and she will gladly give you some options, forward and aft of the jibstay, even if there is no chance you'll be buying a sail from her. Her shop number is 360-385-1640.
Fair leads,
Brion Toss