95% of our flights are just two people (~350#s), but we do occasionally take friends and family up. 4 pax would be all we need.
We do make quite a few "hamburger" runs of about 150 miles, but we also like to take 1-2Week vacations and see places we have never seen before. Plus, we fly to conferences for work which may be anywhere in the Country. I suppose we make about 5 or 6 trips a year greater than 1,000 miles.
We also plan to retire in the near future and expect to make even more cross-countries for the first few years.
We'd like to be able to go Coast-to-Coast in two days. We'd like each leg to be at least 500 miles and take less than 3 or 4 hours.
And we want a reliable airplane that doesn't need a lot of work and doesn't keep breaking down. Our 172 pretty much fits this criteria, and it can easily carry 4 adults with (some) luggage, but it is just too slow for everything else we want to do.
You seem to have a better handle on your needs than most!
With those kinds of trips and time requirements, a 172 is definitely not your long-term plane.
I had very similar needs, with a 1-day requirement from El Paso to the NY area.
The one thing you didn't put down was your budget. I ended up zeroing in on an early M20J, and the older Debs and Bo's. Was interested in the single Grummans as well, but they didn't have the high altitude performance or range I was looking for, and 182s were too slow for the fuel burn.
Flew a Deb and the Mooney repeatedly, and ended up with the Mooney. Could have gone either way, but I liked the additional efficiency of the J, and the cramped entry didn't bother me or the family.
Love the long legs, too. ELP to Chicago is over 1000nm, and I have done that non-stop, when the winds are right, on 64 gal tanks. With that kind of range, I can take on some really large diversions (think multiple states away) around weather and still make my destination. That wing also has a service ceiling of 18,800' at gross, and in the 20's light.
Overall, very happy with the purchase, and would likely have been so with the Deb as well.
You may want to make up a spreadsheet with the GPH, Cruise speed, and ranges of the short list you are looking at. You can quickly generate a fuel cost/mile (a Bo or J is
much more economical over those distances than a 172).
See how long it will take you to do your trips with fuel turnarounds, and what those flights will cost you in the planes you are looking at. It gave me a much better idea of what I needed to purchase, and for me that required sucking up the gear.