Hi John,
I'd say a used spinnaker for cruising may be the smartest sail you could buy.
Here's the selection for a std E38 (not E381 - shorter mast) from Bacon's in Annapolis:
http://baconsails.com/search/boatsp...=50.00&boat_j=16.25&boat_p=43.25&boat_e=14.00
Many boats have them and they get little use, or they were raced/used by the previous owner (and crew) and are now available because the new couple doesn't use it. Getting close in size (larger or smaller) is no big deal if cruising.
Practicing hoists, handling, getting twists, even using a sock will be less stress full with the $500 used spinny vs a new $2500 sail.
I have 3 symmetrical chutes from old racing days and an old cruising assym. in a sock. The symmetrics are bigger (standard PHRF racing rules size) and the pole lets them fill closer to dead downwind. They require a couple of people to gybe but it can be done solo with skill and technique. The cruising assymmetric I use solo because I can gybe it easily with autopilot. It looks smaller to me but I have not actually measured it.
A couple of questions you need to answer:
What wind conditions do you primarily plan to use it in?
You'll get the biggest benefit in light air. You can reach pretty effectively with an assym. in addition to going downwind. If you use a small headsail (100-135), you'll get more use reaching than I do with a std 150% genoa. Above 15 knots broad reaching, the additional speed over my 150% genoa is not worth the opportunity for mayhem when I am solo. I would try it with a crew of two (and autopilot) if I were going a longer distance.
Shorthanded (2 or less) or crewed (4 or more)?
Hard to work the pole and a symmetric during a gybe with less than 4 on a boat as big as the E38. Do you already have a pole? Don't need it with an asymm.
What size (largest) headsail do you generally use?
An asymm can be used tight reaching to reaching in light air so the extra area is a big bonus if you use a small headsail.
Do you like to sail in light air - or do you motor? How much light air do you get?
You'll get more sailing with the spinnaker OR you'll have less time to use it if you skip sailing in 0 - 5 or motor.
A lot of design work has gone into asymmetrics over the past years. I would think for cruising shorthanded (2-3 people) a large, light air (0 -12) assymmetric would get the most use. Adding a sock can help avoid issues on hoisting and dousing. Better yet, a top down furler on a removable sprit would allow hoisting the furled spin at the dock/anchor and then switching back and forth between headsails by furling/unfurling while underway.
Mark