Say one has a healthy bit of change in their pocket and wants a new non-pressurized piston powered aircraft for general business, vacation, family travel, which is it? I'll leave the PA46 Mirage out, because pressurization is a trump card, but will leave the PA46 Matrix in.

Here are the contenders that I can think of. Miss any? Left out the C172, DA40, and SR20, good planes, but not great cross country platforms IMHO.

C182
C206
G36
G58
SR22 NA/T
PA46 Matrix
C400
M20
DA42
Edited to DA62
Edited add Seneca V

Don't forget the super comfy, extra sexy TB21-gt!

And it's one of the greatest ifr platform one can find.

Don't forget these guys:

http://www.vulcanair.com/

On that list the G58 Baron is the one to have. (Although I'd prefer an older baron with a lighter empty weight an a G500 in the panel).

But I am assuming a pilot with some skills to handle a twin. For a newbie pilot with a lot of money to spend, the right plane is whatever can be flown at a beginner skill level. 182 or SR22 come to mind.

If money is not an object, twins have more capability and redundancy than singles. It's just rare that anyone comes to aviation with an unlimited budget.

You need to narrow your mission down a bit before you go shopping. How much of a load are you going to carry? How far? How fast? Over what type of terrain? Once you can establish that, you can start eliminating aircraft.

So define your mission first, and be honest, then start thinking about the vehicle that's going to do that for you.

I'd throw the TTX into the mix too for completeness.

If we're talking fast singles for cross country why not a Mooney Bravo or Acclaim?
I think they are still the fastest SE out there. They both come with newer, wider doors on both sides, a completely redesigned instrument panel with all the bells and whistles. And, they are really not hard to handle, realy! No finite airframe life like the current plastic airplane, the interior is like a Bugatti, I've seen the new ones and they're pretty d(*n good.

Just curious as to why they are treated as the "red headed step child" in the industry?

Because the tail's on backwards.

TB line went out of production years ago - never had glass panels.

And DA40/SR20 just as good XC as a 182

You're half right, and I was wrong, the TB line is not produced anymore. BUT they had glass cockpit. G500, to be precise.

if flying night, terrain, over water IMC and actually have meet schedules I would at least want a parachute or another propeller. Baron is the best IMHO

Isn't that a C400?

Good point. Forgot that the C182 is in the speed ballpark of the DA40 XLS and SR20. I do have some x-country time in all those planes. On a budget not bad options.

Good question. Certainly handle well, I like the looks, and they are fast and efficient. Kind of small in the cabin, but so is a Porsche.

I agree with the above except maybe a good Twin Comanche (probably the best light twin ever made for the average pilot) but then again after 50+ yrs and 7 big blow torch ratings (long retired) I don't do night S/E, IFR S/E. I don't do IFR at all anymore (every day is Saturday, I don't have to be anywhere at anytime) anyway, but if I did I'd want multi-engine, multi backup electronics (not 1 vacuum pump), FIKI, pressurization, alt capability, all those good things.
Barring an occasional IFR soiree, even if the tail is backwards, the new Moonies are pretty good performers x-country.