Moving up from an O’Day 34 to a 40 here in the Chesapeake and have some general questions-
* What typical size headsail do you generally use?
* What type autopilot, above /below deck, electric or hydraulic?
Since I usually am solo on my Pearson 37, I only fly my 110 high-cut jib. The boat came with a wheel pilot that was at its limits based on boat weight, so I changed to a Raymarine type 1 linear drive. I've never regretted that decision.
Looking up the O'Day 40 I discovered it is a Mast head Sloop built in the period 1985 to 1989. Mast Head sloops of that era like their Foresails. Big Genoa's and the crew to manage them.
We now consider a 170 Genoa an extravagance of sail on a 40 foot boat. Who can sail with 6-7 crew on a couple of nights cruise over a long weekend?
New and more modern sail plans look to smaller foresails and better design. Certainly, like @kappykaplan suggests a 110% is a more manageable sail for Solo or Short crew cruising. The 135-140% range with a decent plan to reef and effective furling to maintain most of the capabilities of the foresail gives you a bit more power options. The high-cut design will become beneficial in close quarters with other boats. Unless of course you enjoy managing the helm from the lee side... (like I do). The deck sweeper foresail has little value, in my thinking, for a cruise boat.
On Hadley, this year, I have a 90%, a 140% and a Gennaker/Asymmetrical. Two sails to replace my 155% aged foresail. I have used the 90% over the past 5 years while solo sailing in strong breezes. It balances the boat well and is manageable as a solo sailor.
I am itching to experience the two new sails on my boat.
I upgraded the Raymarine wheel pilot that came with my boat (Beneteau Oceanus 361), which wasn't great, to the Raymarine EV-200 below-deck option. So far I'm loving the EV-200 unit. It was significantly more expensive than if I had gotten a new wheel pilot, but I didn't want to be on the upper end (in terms of boat weight) of new current model Raymarine wheel pilot, which is why I splurged on the below-deck unit instead.
Our O'Day 40 came with a 155 genoa. It was a lot bigger than we wanted for casual cruising. We replaced it with a 135 and are much happier.
Our boat had an Alpha 44 autopilot. Below deck electric ram that only draws .5 amps average. The electronics have gone flaky so I've bought a new control setup from PYpilot. Cheap but sophisticated. I hope I can get it hooked up soon without too much trouble since I'm not any kind of electronics geek.
You hail from Annapolis on the Chesapeake Bay.
Your boat has a listed Displacement: 11,500 lb / 5,216 kg.
Unless you plan to sail her on long open ocean voyages or in violent storms on the Chesapeake your boat would be well inside the specifications stated for wheel or tiller pilots.
The EV-100 wheel pilot comprises a fully enclosed wheel-drive for simple installation and superb autopilot performance.
Quick and easy installation
Fits most types of wheel
Simple robust clutch engagement mechanism.
Maximum recommended laden boat displacement: 7,500kg (16,500lbs)
Revs per minute (rpm): 9
Connections: STng (x1), NMEA 2000 with adapter cable
There are good reasons to upgrade beyond the wheel pilot, they do not apply to the majority of boat owners. Evaluate all the options and your intended and actual uses for your boat. Then prioritize your Boat needs from boat wants.
As an example: Is it better to spend $3400 on a Robust auto pilot to steer the boat in gale conditions or $1200 on a wheel pilot that will serve the boat use under 90% maybe 95% of my boating experiences and $2200 on a new sail to power the boat?
Take a look at PYpilot. Could save you a bundle. You only need to buy a tiller arm and electric ram. The tinypilot computer and motor controller are less than $200 and include very sophisticated electronics.