If you bought it for racing and aimed at $80k outcome you'd be doing pretty well. Sails alone would be worth a fair slice of that. I wouldn't touch it for cruising though especially with that deep keel.
Just my 2 cents. my s&s 39 had 8mm short link and pretty much always laid out at 5:1 whenever I could. She was 11.5 ton empty. Carried a Sarca 25kg with a swivel and slept well at night. If a blow was coming in I'd let out as much chain as possible. KISS method.
Most of my sailing has been single handed on boats from 34 to 47ft mostly mono hull. I learned mostly by myself on how each boat handled but the key was practicing everything on days when weather was favourable rather than jumping into the rough weather and worrying about it then. Be it anchoring, picking up moorings, reefing... practice in gentle stuff first. Ideally yes all lines to cockpit but I've had boats without that too and with a good system in place like autopilot, jack lines, harness etc it has never been a problem in the rough stuff to place a reef in at the mast. Just depends on how your familiarity with the ocean and rough stuff is. The concern from the Mrs is probably lack of understanding on how it all works. It's daunting and 38ft seems big to a novice sailer especially one who just sees tipping and "ropes" everywhere as the default fear setting so maybe a course would help her there or a few club races?