The first thing I think you need is a way to get the boat to steer itself for at least short periods of time if not continuously. I have been working on a few self-steering systems. See my self steering page for details. Basically it is a finely adjustable tiller lashing. An autopilot is a good addition but a bit pricey. I think you need the 2nd tier of autopilot to properly handle the boat and they run in the $500-$600 range. I would get one that had NMEA connections, had a wind drive option, and could handle a boat 50% heavier then a P26. Sometimes when I'm motoring and need (or want) to be on the foredeck I set up the self steering unit and loop each jib sheet over the end of the tiller and around the backs of the winches. From the fordeck I pull the port sheet to steer right, the starboard to steer left. This works great for tweaking the course while handling the headsail or just getting away from the engine noise.
Winches & Sheet Control
Self-tailing winches are nice to have but are very costly ($600-$800 for a suitable pair). My P26 has #8 1 speed Lewmar's and I have always found them to be plenty of power for all my sheeting needs (unless I am flying too much sail, but then the problem is not with the winches). If I were to upgrade to self-tailers they would be #16 (unless I came across a great deal of course). I added a simple pair of cam cleats ahead of the winches to take the jib sheets after they come off the winch. It's easy to put the sheet in and they are out of the way in a spot on the coaming where you can't sit anyway. The cost was a bit less then $40. The cleats can handle about 400lbs. There better not be anything close to that coming off the winch. I added the cam cleats recently and so far they have been excellent. I should have done it years ago.
Lines Led Aft
It is usually automatically assumed that to singlehand you must run all lines aft (halyards, topping lift, reefing, vang, etc). I do think there is some advantage for singlehanding in leading some lines aft but there may be some that are better left at the mast. For those that are run aft I would want to maintain a way of handling them at the mast (keep some cleats and a winch on the mast). When I drop my asymmetric spinnaker I steer off on a broad reach with the main out and spinnaker sheeted in so it collapses in the lee of the main. I release the tack and bring it down at the shrouds. Having the spin halyard led aft would make this operation more difficult. Headsail changes are also more difficult if you need to run back to the cockpit. And I don't see much utility in leading a halyard for a roller furling sail aft. You just end up with a big coil of line in the cockpit that you never touch.
A roller furling can make singlehanding a lot simpler. A good reliable unit with a sail that is partially reefable seems to me to be a good way to go. I think a 130% is a good size sail for a roller on the P26. It could probably roll down to 100 or 90% fairly well. As you roll in a roller sail they tend to get a bit baggy and the center of effort is a bit higher then you typically want for a small sail. They are not terrible good upwind partly rolled either. When they are rolled way in they seem to be pretty flat but the center of effort is very high. I am a bit skeptical of rollers for those new to sailing. It does make things easier but I wonder if these new sailors will ever learn to tie a bowline or learn to work on the foredeck underway. And when a sail change is required they are working with much less experience. And there is the cost. A good roller and proper roller sail could set you back around $2,600 for the P26. That's out of my price range but I wouldn't reject a boat that came with one.
Tuff Luff Head Foil
Instead of a roller furling I put on a Tuff Luff headfoil (#1206, about a 30' length) for about $400, and another $100 to put a luff tape on each of my headsails (3 of them). The Tuff Luff has twin grooves and uses the same luff tape as a roller so I could switch over someday without additional expense on my existing sails (except a uv strip for the one I leave on). The leading reason I got the Tuff Luff was so I could do running headsail changes. The P26 main is pretty small and the boat is typically underpowered without a jib. I can raise the new sail on the inside of the old, tack and drop the old sail on the inside of the new one. In some situations I can raise the new sail on the outside and drop the old one without tacking. This is all done with lots of control and little loss of speed. I can also run double headsails for downwind sailing. The Tuff Luff may not be right for everyone but it works well for me.
Bringing the Headsail Down - Jib Downhaul
With a hanked on headsail a downhaul can be rigged to bring the sail down from the cockpit. You need about 60 feet of line. Tie it to the head of the sail with the halyard, lead it through a block at the stem fitting and back to the cockpit. When you're ready to bring the sail down you take the boat head to wind, release the halyard and take in the downhaul. The sail will come down on the foredeck. It might be good to have some netting on the forward lifelines to keep the sail on the boat. I don't use a downhaul. When the luff of my headsails comes down out of the foil there is nothing to contain it. I have brought the headsail down while heaving to and while locking the tiller while head to wind. I have a double length of shock cord tied form the forward stanchion to the base of the pulpit. On it there is a plastic hook that I set on a small padeye on the other side of the deck.
Lazy jacks are a way to contain the mainsail on the boom when it comes down. Lines are run from a point on the mast (about 2/3 of the way up) to the boom, sometimes multiple points. I think the P26 boom is short enough that one point will do, about 4 feet aft of the gooseneck. There is an elastic section on the lines so to keep them form interfering with sail shape. When I have crew (even 1) lazy jacks seem unnecessary, especially with the full batten main which flakes quite nicely. But for singlehanded lazy jacks seem to have a lot more utility. With lazy jacks it might make sense to run the main halyard and topping lift aft to the cockpit. I plan to try them tied around the spreader mounts to a point 4' from the gooseneck.
I have set up single line reefing on my mainsail. The line ties at the end of the boom, goes up through the reefing clew, down to a cheek block on the port side of the boom, forward to a cheek block, up to a block attached to the reefing tack and back down to a cleat on the mast. I will run this line aft to the cockpit if I run the main halyard and topping lift aft.
Boom Vang/Rigid Boom Vang
My boom vang is a 3:1 tackle that terminates at the boom in a fiddle block with a cam cleat. It is easily reached from the companionway. A rigid boomvang lets you do away with the topping lift. One less line always makes singlehanding easier. There are several types. The main on the P26 is pretty small and there is a fiberglass unit called the Boomkicker that works like leaf spring that might suit it well. I have heard of successful installations on 30 footers. With this unit I would retain by 3:1 tackle system which I also use as a preventer by attaching it to the rail or to a cabintop padeye.
Boomkicker Web Site
Boom Brake/Jibe Controller
A boom brake is a device that attaches to the boom and dampens or brakes the movement of the boom by friction on a line running across the boat. I like the idea of this but am a bit wary of making things overly complex on the boat. But boom control in windy running conditions might make this a worthwhile trade off.
The asymetric spinnaker is almost as easy to fly as a genoa (and easier to fold). And it's a heck of a lot more powerful then a genoa. In light air (5 knots) at 150 apparent we can make 1.5-2 knots with the 150 genoa. With the asymmetric we can make 4. To raise the sail I let out the main and steer about 150 apparent. I raise the sail in the lee of the main then scurry back to the cockpit and head up to fill it. To drop it I sheet in the asymmetric, sheet out the man, fall off until the asymmetric collapses, release the tack and gather up the sail just ahead of the shrouds. This takes just a minute.
Engine Controls and Handling Under Power
The P26 engine is nicely located in a large engine well in the center of the boat. Access is about as good as it can get for an outboard. After 7 years with the boat I fell no real need for inboard mounted engine controls. I can reach the motor handle while holding the tiller when I sit aft in the cockpit. The shifter is a bit harder to reach but not a problem. The P26 is very easy to handle under power. It backs very well and you can spin the rudder 180 degrees for even more control when backing long distances. The outboard can be turned which give very tight turning in crowded spaces. It is pretty easy to turn in about a boat length.
Heaving to is something every sailor should know how to do. For the singlehander it is even more important. It can provide a way for you to let the boat tend itself while you take care of a repair, consult your charts, fix your lunch, or visit the little singlehander's room. The P26 heaves to very nicely. This is how I do it: I slowly bring the boat up into the wind and, once I have slowed to less then 1.5 knots, I tack the boat without releasing the jib sheet. I let the main run out all the way and secure the tiller to leeward. With a little tiller tweaking the boat will zigzag and drift downwind at a very slow rate (maybe .5-1.5 knots). The ride is very stable.
Have you thought about dock lines when singlehanding? I have a 25 foot bow line and a 20 foot stern line. I can get off the boat at the shrouds with both lines in hand to control the boat. Sometimes I tie them together so I can't loose one. When I come into my dock I have a spring tied to the midship stanchion base. The spring has a large loop spliced into it and it is set at just the right length to act as a brake from the cleat at the end of the dock. When pulling up to the dock I step off with all three lines, throw the spring loop over the cleat, hook the stern line around the same cleat and walk forward hitching it to a mid dock cleat temporarily, and secure the bow line. Then I go back and put the stern and spring where they belong. When sailing singlehanded I leave the dock lines in place. I bring the bow line aft along the coaming and tie it around the base of the shrouds, I bring the spring over the coaming into the cockpit and down the companionway, and I coil up the stern line in the engine well. This way they are out of the way but ready to go.