I bought the boat specifically for shorthanded sailing - primarily point to point, or all-day-long distance races. The great thing about the boat is the relative sizes of the main and foretriangle. As we all know, the main is HUGE, so a very large proportion of the drive comes from the main. That means you can use a 125% or 135% jib for your light-air headsail and you don't give away a lot. The spinnaker is completely manageable, solo up to a relatively high windspeed. If your 125% is built a bit on the heavy side, then in fact what you'll do to change gears when the breeze picks up is reef the main, most of the time. If you use a 95% or 100% headsail, then tacking is easy. With practice you can control the tiller with your knees and butt, and hand-trim the jib sheet in 95% of the way by hand. Then settle the boat down and crank in the last 6 inches when you can.
Regarding autopilots....the RayMarine ST1000 and ST2000 can certainly drive the boat. If I were daysailing and only needed the pilot for an hour here and there, in smooth to "moderately boisterous" conditions I would probably opt for the 1000. If I planned to take the boat out to the middle of one of the Great Lakes for an overnight, and maybe sleep for an hour or two with the pilot driving....or do more than that I'd opt for the 2000. Two, ST2000's got my Santa Cruz 27 to Hawaii, singlehanded in 2008. However, a very accomplished singlehanded sailor out here in California has developed a new tiller pilot which by all reports has the RayMarine products beat. All of the 30 foot and under boats in the 2016 Singlehanded TransPac used it.
http://pelagicautopilot.com/
What else? Self-tailing winches really help when tacking, but aren't absolutely necessary because the headsails are pretty small. Get a biggish second reef in your main, that's what I'd say.
I just bought a used Harken ESP furling unit off of Craigslist. I thought this over, hard. The Hood SeaFlex furler was the other choice. ... about $700. The Hood SeaFlex uses an ABS plastic extrusion with a stranded steel cable molded into the extrusion for the foil. It's "aerodynamically shaped" and uses a #5 tape. If I were trailer sailing and I wanted a spiffier unit than the CDI Flexible Furler that's what I'd get. You can adjust halyard tension with the SeaFlex...no can do, really, when underway with the CDI. I worried about the two units, the ESP and the SeaFlex because both are single-groove foils. That means I can't do inside/outside sail changes. Nor can I run twin headsails.
Well, the truth is that I'm never going to do a singlehanded inside-outside headsail change. I've used Tuff-Luffs for years and when crewed, we very rarely do them, but solo...I just don't. No loss there. I do kind of miss the possibility of running twin headsails, but to do that right, I'd be at least double-reefing the main. Well, that will kill the main "engine" on the boat! It didn't make sense. I'd rather run wing and wing, and if I just HAD to run twin headsails for some reason I'd probably make a pair out of 2.5 ounce nylon and stitch them together on a single tape. So I decided that the ESP would work fine. Note that it takes a #6 tape.
You might also consider looking at the Plastimo furling units. They're 40% less expensive than Harken, new and Plastimo is a well-known brand with a bazillion units installed all over Europe.
BTW, I essentially never use a partially-furled sail. It's not a "reefing" option to me. Where the furling shines is in making the headsail "go away" fast, like during a singlehanded spinnaker set...and then making it re-appear again quickly after the douse without having to go forward. I've lose races because I had to go forward to help feed my headsail back into the prefeeder during a hoist, while my competition just unfurled a headsail.