I think this would make an excellent topic for chat, maybe even a blog posting, but I don't think that it's a good fit for a "Q&A" topic on the main site.
This question is insidious because it ticks every box for "Great Subjective Question" on Jeff's blog posting:
- You can give great "Why" and "How" answers
- You can write long, detailed explanations justifying the above
- It's impartially worded (Not "Which is better, X or Y?")
- It "invites sharing experiences over opinions" (though to be fair it kind of invites both equally)
- It can be backed up with facts and references (aircraft specs)
Despite that I still think it falls into the "bad subjective" end of the opinion-based pool. There are just too many possible aircraft that fit any given mission, and a lot of the choice comes down to "Which do you, as the pilot, like better when you're flying it?"
The best we'd be giving someone is a list of aircraft to test-fly.
(In this particular case the Cessna 206 (Skywagon), Cessna 210 (Centurion), Piper PA-32 (Cherokee Six), and Piper PA-46 (Malibu) all sprang immediately to mind - they all fit the mission described with varying degrees of (excess) capability, can be had (used) for well within the stated budget, leaving cash for upgrades and nice-to-have features. I could convincingly argue that every one of these is "The Right Plane For Someone" because they're all good, solid aircraft.)