Seaworthy Headsail Combinations?

I wish you'd post a picture of the boat. Some bowsprits just beg to be a cutter. I'm assuming that this is a cruiser with the rig slammed forwards so it will hang at anchor like a duck. (keel moves forward with rig, CLR moves with keel, windage remains where it was.)

Having said that, on a 30'er, unless it was just crazy heavy, I'd go with a sloop.
I single handed a Cal 28 for about 5 years, and set it up like a big dingy.

You want the ability to change the height of the sails if your jib blocks are fixed. To that end, your standard lapper should be about 2.5 feet shorter on the luff than the available hoist (that's after you account for the pulpit). Use a 4:1 downhaul to tension the jib after the halyard is made off. (Like Gonzo, I despise cockpit led halyards on this size boat. But the little downhaul can be led back if you wish.) I used a recycled and much abused Snipe jib for a heavy weather sail. I fitted a boom to the bottom and ran the sheet from becket to deck to block then forward to a second block on the jib boom then to the deck and aft. This was self tacking, reefable, and could be flown anywhere from deck sweeping up to about five feet above the deck using an extra little pennant wire. One trick I found was to leave the upper hanks unfastened. This let the luff fall off, keeping the jib very flat and highly loaded and balancing the main better. My mainsail boom was also on a track so I could tie in a reef and run the boom up 2'. Very handy feature.

And a light air drifter would be icing on the cake.

Order of business from light air to heavy was-

1. lower height of lapper.
2. reef main and hoist boom all the way up.
3. loosen halyard and lower boom to bottom stop.
4. swap to boomjib, flown fairly high and flat.
5. lower jib and scandalize rig as needed.

That's only one trip to the foredeck for five different sail plans. Only 3 feet of track and it is mounted on the mast for the boom.