@@@@Is my car in any way typical?
I think that a higher top gear or diff ratio would be beneficial. Some folk in the USA are making 5 speed conversions using VW bits. That might be the way ahead.
Your car is typical in that we are carrying out more engine upgrades these days and the spec looks good, although (in my opinion) it would benefit from Late Heads or maybe (?) Zenith Carbs.
The crank is interesting, the rumour on the street is that they always fail – although I have little experience of them, Bob Garretson always said that the fault lay in the width across the Little End – there is insufficient clearance between the rod and the Piston. This is something that is easily rectified and maybe yours was already modified in The States
As for Gears - I run a high top in my (Bog Standard) `C` and it is a great motorway gear. The only problem is that it is a little noisy and you have to suffer the longer drop from 3rd to 4th. I do not worry too much about these things and anyway I deaf.
To set the correct Toe-in on the rear of a 356 (which is mega important) requires the Transmission to be of the correct length from the Output Shafts to the face of the Front Mounts. The 5-speed boxes in The States use their own case so this point would need to be checked. I know of no way that you can get another gear inside a 356 Case without a different Syncro. system or the use of Dog Rings
In my opinion the better way to alter the gearing is by fitting a higher ratio Crown-wheel and Pinion. This raises 4th and 1st which are both a little too low and, of course it does this without altering any of the drops between the other gears. I have a transmission built but have yet to find the time to fit and trial it.
As for Max Speeds – I am sure that Will, will correct me but I believe that the Bill/Will Stephens Speedster is touching around 130 mph before they brake for the 2nd chicane on Mulsanne.
As for me – In the Tour Auto, on a French Auto Route, I saw 140mph (slight downhill with the wind behind me) in my 356 Carrera GT (that was approx. 7,600 rpm) - I was then blown away by a GT 40 who must have been doing 200 +
By todays standards the cars are noisy at speed but a lot of it is wind noise