I see this a lot in my business (Motorcycle, Watercraft and Jet Boat dealership) and in most cases it's ego, pure ego.
When I was 12 my dad (an air force officer) was stationed at the old Newport RI Navy base for a year. They had a sailing class for military and their families. It was more like basic training. Final exam was to singlehand one of their 26 footers from the slip, around the bay and back into the slip, these boats had no motors. So, I had a good base of understanding when, a year later and now living in Finland, we got a 23 footer. I spent just about every summer day sailing for the next three years.
Years later, now living in Florida, I got a Hobie16. What a fun boat! I think this is one if the best boats for learners. So easy to set-up and sail, and always fun. The Hobie gives you instant feedback and lets you know if that last adjustment was good or bad. Displacment monohull's tend to be more sluggish with feedback, making learning a little more difficult.
When we decided we wanted a weekender I started looking at 23 to 26 footers and found a Westerly Padgent 23. This boat had everything needed for a family of three for weekending and short vacations. I wanted a "stout" boat and the Westerly is about as stout as small boats get. Owned her for 15 years but she never got as much sailing time as that Hobie.
Now, after a 15 year stint of no boat I've decided to start sailing again and found a 28 footer in reasonable shape for a 40 year old girl. She is more work to singlehand but I suspect that will get better as we get to know each other.
i wanted to buy a hobie 2 years ago, but the wife would not even think about going on one.
That's really a shame because they are so much fun to sail. If you could get her to just do one sail (calm day with little chop) she might change her mind. If you can find an old G-Cat in good shape they are even better than a Hobie for the wife. G-Cat's are nearly impossible to flip (you've really gotta be trying) and have a very usable front trampoline so they have a lot more people room.
Sometimes things aren't as logical as they look. Example: We have many customer's who's wives won't allow the kids on a dirt bike but will allow them on ATV's. The logic; four wheels are more stable than two so they must be safer. WRONG! Fact is, when you wreck an ATV (and kids are always going to wreck) it's so stable it falls right on top of you, just about every time and ATV's are a lot heavier than dirt bikes. A two wheeler will usually pitch you off but will rarely fall on you and if it does it's a lot lighter than an ATV.
There is a joy to sailing small boats, solo or as a couple, that you just don't get on larger boats.