It is hard to beat a '36 DeLux 5 window coupe, of course I may be partial since I have owned mine for 59 years come this September. Actually I have always wanted a '36 convertible coupe, not the club coupe I don't like the short trunk and long doors.
Before I moved to So Cal in '56 from Idaho I had many chances to trade my coupe for a convertible, everybody wanted to get rid of their open top cars when the snow flakes started to fly. My coupe has always had "warm air and sweet music" so it was pretty comfy in cold weather. Since four of the five, actually six including the windshield opened, there is a lot of ventilation from the summer heat.
My second choice would be a '34 convertible coupe or a '34 Vicky. My third choice would be a '39 convertible coupe w/rumble seat.
I never fulfilled my lust for a '36, etc., open car because when they could be purchased for under $400. I could only come up with $350. When they hit $900. I only had $850., in other words, I was always $50.00 short.
In 1996 I was on an old car scouting trip in Montana. Sitting out in a farm junk pile I thought I had gone to old car heaven. Sitting in the middle of a seventy year plus collect of cars, trucks and farm machinery was what I thought was a '39 Ford convertible coupe, tear drop tail-lights and a rumble seat.
As I tried to contain myself, looking at the other cars I slowly worked my way up to the convertible, finally I could see the banjo steering wheel... Damn it had a SAILING SHIP on the horn ring and said PLYMOUTH in the middle of the radio grille.
To make a long story short I was given the car by the farmer, I brought it home to California and over a ten year period I have completely rebuilt the car.. It is not the car of my dreams, it is actually better than anything I could have ever wished for.
Sorry about cluttering up the topic with something other than a FORD.