Wow, deja vu. This is an ongoing discussion on our boat, and has been for over a decade. I also did a lot of signlehanding before LD moved aboard, and I was my safety gear. I had no electronic nav equipment (till LD gave me a handheld GPS she got for free for NOT driving a Cadillac), good ground tackle and an old autopilot was it.
When LD moved aboard, there were huge changes. Not only did I have to get rid of a lot of my clothes (some of which I'd had since 1983 and still miss!), but I just happened to find a woman who wanted to sail with me and darned if she didn't know boats, too, which made her just a little too well-informed for me to railroad. So then discussions about 'safety gear' started coming up, and continues to this day. You and I are of similar minds, Chris, but LD isn't. So we've had some very lively talks about how so-called safety gear doesn't make you safe and insurance is a racket. If I was sailing alone, I'd never have an EPIRB and a liferaft. When LD and I were cruising up north, we didn't have either because we couldn't afford them. Now we're outfiting a bigger boat for eventual long-distance cruising and the questions are coming back up.
I think every singlehander who's lucky enough to have someone who wants to join him (or her) goes through the same stuff. I have a good singlehander friend who just got married and added a watermaker and all sorts of 'luxury' gear to his small boat to ensure that his new wife would enjoy their cruise. I'm lucky in that, as a stubborn asshole set in his ways, I have a strong independent woman who'll slap me upside my head and say, "Listen, this is how we're doing it." And that's apparently the only thing that works for me!