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I just paged through that Yat-Ming offering mentioned above.  For the diesel transitional era, there are some decent 1950-60's cars, but you have to ignore half of them, unless you are modeling a Calif. or Fla. beach party, because they are convertibles.  Many train modelers are rumored to be in the Northeast population centers, where palm trees do not grow.  For my pre-1941 era, the listing is full of Fords....which is not the only make available in that period.  While one of the ugliest Fords (IMO, 1937-38) is offered, and that a neighbor drove until 1955, it is a convertible from Yat-Ming, and the neighbor drove a trunkless coach, which I WOULD buy a model of.   Chevrolet did not even offer a convertible in 1939, but did again in 1940.

The vehicles MTH has cataloged are Yat-Ming. I also like those and recommend checking out Diecast Direct as well. They have a fairly good selection in your price range.

As for convertibles... We have two kinds of weather here in the Midwest, too Hot and too Cold with about one nice day in the spring and maybe another one in the fall. That doesn't deter the convertible folks around here at all, there are plenty of them on the streets. However, most folks do put the tops up in winter and the old bald guys usually wear hats in the summer, at least after the first long drive anyway.

 

Motor Max and Road Champs have made some decent inexpensive 1950's cars, mostly Chevys. I don't know if those brands are still made but you find a lot of them at train shows and toy shows, and on eBay. Somebody made a pretty nice '57 Ford that can generally be had for well under 20 bucks, but I can't remember the brand. Road Champs, maybe. Ertl also has made quite a few steam and transition era cars, including a '49 Mercury and a couple of different variations on '55 and '57 Chevys, including taxis. Solido made a 1950 or so 2-door Chevy sedan in a bunch of variations, including police, fire, and taxi. I have a couple of '59 Chevys, I think those came from Road Champs. There are several different inexpensive models of the 1956 Ford, and if you want to go up a bit in price you can find a good deal on '53-'54 Fords and Mercurys and '56 DeSotos from Collectors Classics (long discontinued, check eBay). And there are mid-50's pickups all over the place.

BK:  Brooklin has fairly well covered Buick, for pre-1941,  but they have done a few others, including a 1940 Pontiac wagon, that I balk at the price for, too.  There is somebody's  red 1936 Buick sedan, but I thought red, as well as another yellow Brooklin Buick, an unlkely color to be often chosen in that frugal era.  The red 1936 model, whatever the brand,  is reasonable.  I do have a 1939 Brooklin Buick that I picked up reasonably. People drove them, so I would put a few Buicks, not in droves, as I won't the Fords, on my layout.   Years ago, I looked at a real 1939 Buick sedan that was for sale, and more recently had a chance to bid on a,  to me much more desireable, 1940 base model Buick coupe.  This last was in an unadvertised estate auction so could have been bought reasonably.  But, of course, it wasn't a LaSalle.

Road Champs is no longer made. They did make several versions of the 57 Ford...plenty of police cars that you can do a make over and turn them into a civilian 4 door sedan. They also made several versions of a 49 Merc, 55 Pontiac Safari wagon and plenty of trucks. I think some people are turned off by the cheaper Ertl cars and don't know they made the better American Muscle series.

Bob

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