Ease into it and you will be fine, start off just playing with the toys at the
dock, then just
motor around a little while and pay someone to help you
dock, pay for that until your sure you don't need it anymore,
docking is the hard part, or I think it is anyway.
Just remember, you can't stall a boat, you can simply stop and take your time to think about your next move, Sailboats are SLOOOOOW and that is the appeal to me.
Buy towing
insurance, you already know 95% of
radio useage.
Just never, ever, not even once raise your voice to the Wife, make her very comfortable with the boat, make it her comfortable place, her happy place or strive to. Start out on those windless Summer afternoons just barlely motoring around, letting her watch the Sunset, strive for a stress free experience, save the rail in the
water sailing for later.
Stress and apprehension is a huge issue with seasickness, fatigue and I assume her pain issue
Take your cues from her, if she is uncomfortable, stop. There is tomorrow, no schedules on a boat
Trust me, happy Wife, happy Life. If she likes it, you will get to spend a LOT of time on the boat, if she doesn't, then you may not.