Have you considered an A320? Cockpit is super comfortable, performance isn’t bad, and getting coffee enroute from the lead flight attendant is a nice touch.
I would love to buy my last plane first, but a PC-9 is a little out of the current Rich budget. I am cautiously optimistic for future Rich though.
My first bird was a 68 Piper Cherokee 140. At the time it had a just been rebuilt with 160 HP, new interior and 5 year old paint. I paid $42k in 2004, sold it for $32k 14 years and 500 hours later. It was a good trainer and XC airplane for 2 or sometimes 2+2. I only carried 4 people in it one time, but my wife and I took many trips in that little bird. We could do 400 NM in a single leg if the wind wasn't in our face. It's worth a look if you can find a good one.
all the mentioned birds have advantages & disadvantages. If buying a 172... get an older one (payload is much lower on newer models). If you want to go looking into experimentals... how about a RV10? Tobias P.S: High- vs Low-Wing... you could just as well start an oil-thread
Of course If I won 50 Million, I would have a 206 on wheels, Kodiak on amphibs, and some super STOL dragger, maybe a Maule, or cubcrafter cub.
Tip of the day: Buy a C130 - and you have enough space to take each and every aircraft for tomorrows mission with you at any time (tip 2: that way you only have to rent one hangar... )
Confession, I haven't officially flown anything that isn't piston, although unofficially have about 30 hours in a turbo otter on floats. I haven't flown a twin in a long time, and those were only an Aztec and Chieftain. A C 130 isn't even on my radar to buy, even if I won 50 billion dollars.
Ok, if I had 50 billions of USD I would probably go for a rebuild of the AN225 - and would chuck the C130 into the cargo bay... true (having said that... there are better things to do with life than buy twitter....)
Bonanza …. someone had to say it 2 people. 172 or Cherokee are good but currently expensive choices. If you want more simple and vfr only that opens options too