Yes, when the Auto pilot quit on me.... but I dealt with it... that's what makes single handing so rewarding.. figuring things out ahead of time so the true emergencies are rare. The biggest issue with single handing is how to get enough sleep.Let's add this question: Has anyone, while single-handing, had a situation arise where they wished crew aboard?
Here's the deal.... keep your wife happy... invest in a good harness and tether.. wear it.. stay clipped on... even in the bay or marina. Invest in as much anti collision gear as you can afford... an AIS system for instance. Keep a handheld waterproof VHF radio clipped to your pfd.. besides a good quality fixed mount. .....
For your wife's peace of mind... invest in a personal locater device such at a SPOT
If you don't have roller furling... rig a jib downhaul. Practice reefing at the dock..
By all means... invest in a reliable auto pilot. Might be the most important piece of equipment you'll own.