New here! Looking at some different planes and need some help!

I don't quite understand your point.

That a Cirrus might be more acceptable to his passengers?

From what I understand he and his son are pilots and they are looking for a plane for them that can occasionally haul 4 200lb people and (I am assuming) some room left over for bags. 500 and 1000nm trips were mentioned so I was thinking something in the 150kt+ range

You are correct. The majority of use of this airplane will be solo/dual but used enough hauling 3-4 people that it makes sense to get a 4-seater while traveling up to & around 1,000 nm. 150kts would be nice (that's a LR cruise speed, not the max speed though).
 
Doesn't really matter what he's comfortable with, only what they're comfortable with. I've seen numerous pax "drop an A-36 like a hot rock" and head en masse for the SWA ticket counter because of all the obvious reasons (size, space, speed, amenities) that everybody who considers such a plane should anticipate but that the plane owner thought were OK and they would adjust to them.

I'm comfortable with most seats for flying. BUT, if I have a choice as I do now, I would like to get a nice plane that has a comfortable seat. The passengers I carry (wife, son, daughter and the occasional friend) wouldn't do that. From where I am, it takes an hour to get to the airport that serves ATL, DTW, DFW, etc.... Here's an example of a trip to MIA.
- Drive to airport at 5 am (1 HR)
- Flight with layover arrive at 11 (5 HR)
- Cost per-person (Just under $800)
So the total time it took to get to MIA was 6 HR and $3,200. If I were to fly by myself:
- Drive to local airport whenever I want to leave (10 minutes)
- Cost of fuel $1,500 (RT)
- Flight with stop (Around 5 HR)
So, we would still be traveling about the same amount of time. The difference is that we could pick the time of departure, etc... and etc.... Cost would be around $2,000 RT (factoring AP cost and all the other "amenities" associated). In my eyes the convenience of it is too good to pass up even if you can't get up and go to the bathroom or stretch your legs out all the way and my wife agrees. My kids on the other hand haven't given it much thought yet, they think it's too cool that we could just fly down to MIA for a weekend (not gonna happen BTW).
 
I wish I had that dilemma :D

Haha. It's not really a dilemma. It's more like, I wish I had that money but I don't. The money that I have I have been saving for close to 10 years now for a plane. My son has been drooling over the Pilatus PC-12 but I told him no. He's flown in one (local airport had one fly in while my son was taking lessons and the owner/pilot was grascious enough to let him sit in on a flight around the pattern while he was waiting for his passengers to arrive). He came back all excited and couldn't stop talking about it. I too drool over the plane but it's WAAAAYYYY out of my budget. $4 million for it is not for me unless at least another 5 people were to get in on a deal and then I would jump all over that!
 
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