[Ajax_MD]

This is a vague question with no concrete answer. It depends on the boat, and how it's setup.

A 25' boat, with hank-on headsails, no tillerpilot or tiller clamp, and no lines lead to the cockpit can be a real PITA to singlehand. On the other hand, Bene505 singlehands his 50 foot Benetug regularly. His boat is probably extensively setup for singlehanding.

Generally speaking, I'd say that it's common to singlehand boats up to 35 or 40 feet. That's just a vague generality.

 

[Ajax_MD]

Single handing and leaving the cockpit. Not a good plan.
Jim

That's your threshold of risk. Some of us feel otherwise, especially when geared up with an auto-inflating PFD and jacklines.

 

[Ajax_MD]

Now that is just rude.

All in good fun. Bene's boat is very nice, and he's a really cool guy with a lot of good ideas.

 

[Ajax_MD]

Thats the same scenario I'm in....She has made it clear she won't be "sailing" while she is there...Although she already mans the tiller and steers while I man the sheets...

So whether she's onboard or not, you'll essentially be singlehanding. You would be surprised how much more boat you get for only 5 more feet, LOA.

Several thousand pounds displacement, a smoother ride (depending on the design) and oodles more cabin space. The operating and maintenance costs will increase too-

More hull area to paint
Bigger, heavier sails
Longer, thicker control lines and halyards
More deck hardware
More expensive autopilot (if you decide to equip one)

My opinion is that you don't need to add 10 feet to please the wife with a smoother ride. You could probably go 5 more feet. I guess it really depends on her.