I have no dog in this fight. Nor do I have a ton of experience in most of your choices. Typical internet know-it-all jackass. BUT at least I admit it!
Trinidad - always liked 'em. I have only sat in one. Liked the comfort and vis. Performance specs seem promising if not world-beating. If you have a trusted Socata shop nearby, so much the better.
Mooney - have sat in one real 201J, not in flight, and a factory Acclaim mock-up. More of a sportscar seating position but roomier than it gets credit for. Do not like the USPS mailbox-slit door nor the clean-and-jerk height baggage compartment. Again, performance specs look good, plus likelihood of A&Ps having exp higher tham TB21. Parts probably cheaper/easier to obtain.
Cirrus - Only flown a -20. Modern sportscar (Porsche) interior feel. Very non-airplane! Mx and svc support likely much easier than either of the previous 2. If you aren't a chute-pullin' dope, who cares aboit the stigma? It is still there in a pinch. For thise who cite the 10 yr repack, well, if you can't do the time don't do the crime. Every plane has its own financial idiosyncracy. My reservation would be with the post-crash fires. Mooney is stout without the fireballs. Or pull the chute...
Anti-Cessna - probably didn't read your post carefully enough. I know that you are big. I get the claustrophobe thing, but....much better sightseeing in a high wing. Plus you are sheltered from rain when loading and sun when flying. The 182 is an excellent jack-of-all-trades that you may wish to reconsider. Turbo, non-turbo. Old, new. Retract, non-retract. Glass, steam. Something for everyone, a bajillion parts available and virtually every A/P has worked on one. Short fields. Grass fields. Class B megadromes. You can get in anywhere, hauling a decent load, without risking an extensive downtime if a mx event hits.
Sierra - wide cabin. Two doors. 10-15 kts slower at same fuel burn as 182 plus Beech parts prices (and availability). I had a Sundowner. Faster than it gets credit fir and very comfortable.
Bonanza - narrow cabin, imho. I prefer 2 doors. Beech parts prices are Defense Department-level. Great availability, though, and Conti engines that enjoy LOP ops.
Maybe look into a late-model Dakota. Basically a low-wing 182.
Final thought. 200-250 miles typical trip? If you haven't already, figure out the time difference for every 5/10 kts performance. You may be surprised at how little an extra 15-20 kts really matters on your trip. For the record, I have owned a 1983 Sundowner, 2004 T182T, 2008 Matrix, and now fly a Meridian. So, I have been down the 'what airplane is best for me route' a few times.
