When I lived in Burlingame, sailing out of Coyote point on my buddy's Santana 22, a smaller, zero roach main with a suit of headsails was preferred. However, he rarely sailed single handedly, so with 1 or 2 additional crew, changing headsails was pretty cut and dry. As was reefing the main.
Single handing, however, was, and is, a different story. With today's furling technology, I'd have no problem single handing with a quality roller REEFING furler. This would be one that has a multi track, rigid, alloy foil, As opposed to a flexible luff type designed for trailering convenience, or even the hard plastic luff insert with the captive halyard(CDI). Neither of those type furlers allow for effective reefing and are impossible to sail change quickly especially the CDI type. The higher quality furler would allow you to carry essentially two sails. A genoa 120-140, and a jib 80-110. Instead of a padded luff I'd use the sewn in cord insert, much lighter, yet very effective. You can start with the smaller sail, move to the large one if desired.
Needless to say, a reliable tiller pilot is important. A single hander's #1 tool. A single line mainsail reefing system could also be helpful if it takes you longer than say 20-30 seconds to go forward to set the clew line and luff hook.
The rigid foil furlers are less practical on trailered boats, Not impossible, just a bit unwieldly when setting up and taking down. As a mobile sailor, I'd be inclined to go with the hank on system. I would start building an inventory of sails to suit the conditions. I'd go with four upwind sails, #1 genoa, #2 lapper, #3 blade and a #4 storm jib (65-75%). Regarding the #4 storm jib, It might make sense to rig the #4 on an inner forestay and keep it on the foredeck ready to hoist. Rigging a jib downhaul is really beneficial, too. I can't believe how much easier this simple tool makes foredeck sail handling.
Changing hank on sails. A couple things I found helpful.
First always carry a couple of sail ties in your pocket.
Next, store the sails with the hanks clipped to a wire pendant. when you bring it on deck the sail will be in position to make the transfer, new hanks on the stay, old hanks on the pendant. How you manage the halyard, tack and head... and the sequential change depends on preference and whether you have some help. A little practice will help you sort the procedure out. The important thing is you stay organized with both sails. In the end, the old sail will have the luff stacked vertically with all the hanks together... making for a long narrow package (folding pattern will look different than what you're probably used to seeing) that you can simply roll up from the clew, after switching the sheets over to the new sail.
Don't leave sheets attached to sails when storing....which means two sheets, not a single line like you do with a furled sail. If you have movable jib leads and marks on the track for each sail... you should be able to use the same set of sheets for all sails. Use a bowline, it's easy to tie and untie. Overall, separate sheets is more sensible, less work and easier on the rope over time.
Here's a case where having halyards run aft is an inconvenience if you're single handing. If the halyard is at the mast, you can bring the sail up on deck, roll it out in position, step back to the mast and drop the halyard. go forward to exchange the hanks, back to switch the sheets, hoist the sail and roll up the sail, pulling it aft to the foredeck hatch. You're done... just one trip forward. With the halyards led aft to cockpit (like my boat) you would drop the sail first, the go forward with the new sail... do the change, switch sheets, roll up old sail, drop down hatch, then back to cockpit for the hoist. whew! sounds like a lot more work, but it isn't really.
Okay, that was chatty of me... sorry.. hope there was something in there that may help. good luck, have fun.
