Some suggestions to make single handing easier:
1. Electro-mechanical Auto pilot (with additional 'water proof', pocket type, remote control) - allows steering control from 'any' location on the boat, ... including 'overboard'.
1a. Since you'll have an electro-AP (as per above) ..... get the optional mast head steering vane -- boat will hold close to optimum sailing
angles in varying winds - hands free.
Note - OK for just about all wind directions 'higher' than a (125°) broad reach; electro-mechanical mast head vane controlled function doesn't 'do well' for DDW or deep broad reaching.
2. 'Retractable' Lazy jacks - to control the mainsail, no need to tie in 'bunts' when reefing. Example - Easy-Jaxs: Lazy Jack System - EZ-JAX
... lazy jack control lines lead to cockpit.
3. A 'super-slippery' mainsail track - virtually no friction
when raising or lowering. example - https://www.tidesmarine.com/index.ph...egory&path=363
4. Most all sail controls, etc. run to the cockpit - downside is that you lose practice going forward during adverse condition
5. jib/genoa on a reefing-furler.
6. Second (spare) means to start the engine - a 'hidden' push button switch (with 'flip' cover to prevent 'accidental' starts) near the helm station, with easy accessibility for 'instant/emergency' use.
7. full tether and jacklines for use when going forward and additional adequate 'hard points' for the tether AT the helm station ... AND the near the base of the mast
8. Electric anchor windlass ... with pocket remote in addition
to the typical 'foot switches' near the bow.
8a. Anchor wash down pump.
9. large drain near helm station .... so when you 'cant' leave the cockpit, you can still 'go'.
10. An 'over-the-top' leech line for mainsail .... allows adjustment of leech line tension from base of mast or from cockpit. No 'hanging overboard' when adjusting the leech line, especially on a deep reach in 'stink' weather. Arrangement should be such that leech line jam-cleats at each reefed clew position are mirrored along the luff at each reef position.
11. Triple reef added to mainsail ... for when it gets 'real gnarly', or for when you 'need' to heave-to on a 'handkerchief'.
12. Relocate all genoa/jib winches so that you don't have to 'move' from the helm position to adjust the jib sheet tension - just bend over and grind, etc.
13. Choose a 110+% jib ... less snags for when in 'stink'. Easier when tacking, as if you're 'quick
', no need to grind a winch.
14. Self-tailing jib sheet winches if you don't already have them.
15. If you already fly an asymmetrical spinnaker ... a free-flying spinnaker furling system.
There's more; but, the above should cover the bulk of it.