A couple thoughts here, but the specifics of this discussion is extremely dependent on the specifics of the boat in question. For example, a 110% -115% genoa is nearly useless on boat design which has a standing sail plan that results in an SA/D somewhere below 15, while the same percent genoa can be used across an extremely wide wind range on a boat with an SA/D somewhere approaching or exceeding 20. And if that boat is a fractional rig, then the headsail will typically have a wider wind range then the same percent on a masthead rig. The correct sail size is also extremely dependent on the the geometry of the boat and the way it is equipped and sailed. This is where a really good sailmaker comes into play in terms of making the right choice in sail fullness, size and fabric.
If I were in your shoes, I would want the largest minimally overlapping headsail that can be sheeted inside of your shrouds. This will vary with the geometry of the boat. I would look very carefully at your deck plan and shroud geometry. You will find that because of the shroud positioning, there are some overlaps which just are not practical.
Depending on the specific design of the boat, the geometry of the shroud positions will typically make a sail sized somewhere around 115 to 130 percent impractical. What typically happens at some point in the % range is that the shroud layout prevents from the jib from triming inside the shrouds without the sail and sheet laying across the shrouds, and/or the leech of the sail hitting the forward edge of spreaders. By the same token sheeting this same sized sail to the outside of the shrouds would prevent the boat from being able to point as high as she should (Smaller non-overlapping headsails usually have a slightly narrower sheeting angle near the shrouds). Determining that 'no-go' size is important.
The next part of the decision has to do with hardware. You need to see where your deck tracks are positioned and decide whether you would need to add or modify the tracks so that the sail will sheet properly, and if the sails do not work on your existing tracks, you need to ask yourself whether you are willing to make changes. If the deck tracks limit your options and you are not willing to add or modify the tracks, then the position of the existing deck track may limit the overlap (either bigger or smaller) of the sail.
This next item is often overlooked. If the boat has an effective backstay adjuster that can be easily adjusted on the fly so that headstay sag can be easily controlled, and if the boat has efficient winches, which allow halyard tension to be quickly and easily adjusted, and if you are likely to adjust both, you can have the sailmaker design the sail to be cut slightly fuller. This will greatly widen the useful wind range of the sail, because you can ease the halyard and backstay and effectively use the sail into lighter wind speeds and tension the backstay and halyard to flatten the sail and therefore carry it into much higher winds. Proper hardware that is properly used can easily double the wind range of any specific sized and properly cut sail.
But here is where the problem of sail cloth type and weight comes into play. If a small sail is intended to be used at a lower wind range, it needs to be made from comparatively light weight fabric so that it will not sag due to gravity and lose shape. But of course, the whole idea behind using a smaller sail is to be able to sail into a higher wind range, and in heavier air, conventional light-weight dacron fabric will stretch and power up the boat (a bad thing increasing healing and weather helm) and if this light weight dacron sail is used in a steady diet of heavier air, it be short-lived as well.
Depending on the boat, if you wish to achieve a long lived sail, which is also light enough for light air, and low-stretch enough for heavier winds, you will probably end up going with a higher modulus, higher tech fiber and a carefully engineered cutting pattern. This may sound expensive but the better lofts seem to be able to do this kind of thing for not much more than the prices for conventional junk cloth from run of the mill lofts. And these higher tech sails will hold their shape longer, require fewer sail changes, and perhaps eliminate the need for an intermediate sized genoa. ( I have a 111% #3 that Quantum made for me that works very well in a range from 5 knots apparent (1-2 knits true wind) to 25 knots of apparent wind. The sail is a horizontally cut kevlar laminate. After 4 seasons of uhard se it still looks basically new. Because the sail was horizontally cut, the cost was very slighly more than a similar dacron sail.)
In terms of the question about making a sail change short-handed, its all about the tools and techiniques: netting and pre-feeders are your friend. I will first say that there is a huge difference between sailing with a smaller properly cut sail and a partially rolled-in genoa, even with a foam luffs. First of all, foam luffs typially only result in a proper sail shape with the sail rolled 10% to 15%. This still can leave a very big sail and after about 10%-15% retraction there is no control of luff tension, a critical factor in having a practical heavier air sail. But also using a partially rolled genoa as your heavy weather sail with any frequency will greatly shorten the useful life span of the sail. In my experience, a properly cut smaller sail will have the right shape for the conditions while the rounder shape of the partially furled genoa will not quite feel like the right balance between having enough power to deal with the sea-state conditions and still control weatherhelm and heel angles.
While I typically try to pick the right sail for the conditions and have my sail plan designed so that individual sails have the widest wind range possible, there are still times when cruising short-handed that I end up making sail changes. In terms of the tools to make sail changes short-handed a little more easy to accomplish, on my boat, I have netting between the toe rail and top lifeline on my foredeck that allows me to stuff the sail between the rail and lifeline and keep it aboard. (The so called netting is actually 1/8" dacron line which zig zags between the rail and lifelines). When I single handed raced my boat I rigged shock chord with hooks to quickly hold the sail down. I also have a technique of tieing sail ties to the toe rail so as the sail comes down I can lash it to the rail safely out of way in heavier going but end up with a sail all tied up so it can be moved when I am ready.
The trick to the drop is to run the halyard one turn around the winch in the cockpit and up the weather side deck to the bow making sure it is clear to run before releasingt the halyard stop and walk forward with the halyard tail in hand. Sit on the deck with your back to weather and sit on or roll off of the halyard while you lower the sail to increase or decrease friction and make sure the halyard is clear. Pull the sail down from its forward edge and pull it forward and downward into the netting and deck. Tie it off quickly.
The other tool is one or two pre-feeders. Schaefer 76-30 Sailboat Engine Parts and Boat Parts-Torresen Marine
Harken - Sail Prefeeder
On my current boat I use a single roller-type pre-feeder on a lanyard tied at the stem fitting for normal headsail raises. Once you get the geometry right, it really makes headsail raises a piece of cake. When I single-handed raced my boat, I used a second pre-feeder mounted on the rail 3-4 feet aft of the stem and this pretty much guaranteed a flawless raise from the cockpit, (But added some additional friction.)
(P.S. Hesper: I grew up sailing out of Consolidated Yacht yard on City Island. Its a great place to sail from.