For a trailerable boat like yours, what you wish for or NEED will vary depending on your type of use. The decision becomes a priority list based on convenience for your area and your particular usage. As a coastal cruiser doing the occasional 40-50mi sailing runs and week long stays:
(1) I wish I hadn't waited 4yrs to upgrade to self tailing winches.
(2) I finally went for the pricey A-sail setup and could take it or leave it because it's rare to run for too long on the ideal angle or wind speed that it likes(although with continuous line furling from the cockpit our setup is fun and easy to use solo when it's right. pic below).
(3) I sprang for an auto pilot early on and love it! I'll use it for hours at a time for helm relief because we're doing longer runs down the coast and it takes forever to get somewhere at 5kts.
(4) An early priority for our use were mods for an easier trailering experience, huge bimini, pressurized water, larger batteries, good foam for bedding, mast top VHF ant, modest chartplotter and serious ground tackle.
(5) Above all else I suppose most folks compromise on the OB and I'm elated that the orig owner of our boat didn't. 8hp high thrust yama p/t, elec start, alt. The greatest sailors lie/embellish about how much they do/don't motor but man we've used this gem to it's max. I'd say it's almost the single most important asset on the boat.
Hope that was helpful and isn't straying too far from your question. Good luck, Mike