Re: Best Vintage '40s-'50s big outboard
The earliest 50hp with user-friendly bits (.ie electric starting and gearshift) would be the Fat Fifty V4s of 1958, from both Evinrude and Johnson. The 1943 version is an opposed 4-cylinder beast with direct drive and no easy way to hook up electric start and remote capability. With a bit of parts swapping and light fabrication, you might be able to put a '58/'59 Johnrude 35 cowling on a later Johnrude 40 from the 1970s.
Mercury came out with their 60hp inline 6-cylinder in 1957 as the Mark 75, but I wouldn't really characterize these start-in-gear, direct reversing Dockbusters as "user friendly." Neat as heck, but they have many quirks. Mercury's Mark 55 40hp are decent enough motors, less quirky, and not hard to find. Again, with some parts swapping and light fabrication, you might be able to graft 1950s Mark 55 cowling bits onto a 1970s-1980s era Merc 45/50hp 4-cylinder.
An alternative I've seen on several occasions would be to graft a 1950s cowling onto your existing 50hp. Several routes you could go with that. One guy made a plug of a 1956 Johnson 30hp cowling, and used it as a mold. He then glassed the bottom 2-inches of the later 2-cylinder looper cowling onto his giberglass copy, then painted it appropriately to give it the look of the '56. From the water, you couldn't tell, except that the motor didn't sound the part if you're familiar with what various motors sound like. On the trailer, you could tell as the lower end, although it was the right color for '56, didn't look anything like a '56.