Questions from a newbie...

You will probably want the Chevy tranny, the 700R4. This swap has been done several times and there are adapters for to do this. Get this done and the rear end installed, then a custom driveshaft to connect them.
The Dakota tranny can be used too.
With either of these, the 3.55s will be too conservative. 3.91s will be almost the minimum.It depends on your engine build.
But I gotta remind you;you said
I'm not a red light to red light drag racer, so I'm looking at 3.23 or 3.55 gears to keep it streetable.
With 3.23s you won't need an overdrive; 65=2600 with zero slip.
But I then gotta ask, why the 408? I mean that is a competition buster and a tire-fryer.Why build a 408 just to drive it on the primaries it's whole life?

If you skipped the stroker kit, and put the money toward a GVod, You could go to a much smaller engine, and have IMO just as much fun on the street, while reaping the benefits of burning cheap gas and cruising 65=2200. If you swapped to a stick, I already worked out the kinks of that swap for you. Now you can make use of the GV as a splitter.
>Here's how the automatic ratios do while splitting;
the ratios are 2.45-1.91-1.45-1.13-1.00-.78od, Gv in red,
the splits are.... .78.....76....78.....88.....78
This is suitable for the track, if you trap in 2nd over. This will probably take 3.91s, to trap 112@6455. The starter gear would be 9.58,a little lazy. 65 would be 2460@zero slip.You can hit 60 in first-over at about 5850.
> here's how it works with the A833 deep low;
The ratios are 3.09-2.41-1.91-1.30-1.39-1.09-1.00-.78od., GV in red
the splits are.......78.....79....78....*.....78......92.....78 ....... *=not used
This too is suitable for the track, now with 4.10s, but the shifting will be; 3.09-2.41-1.91-1.39-1.09. 112mph will be 6220. The starter gear is 12.67.and 65=2582. You can hit 60@6122 at the top of second using three ratios! Man that is putting down average horsepower.

>For a guy who is not interested in tracking his car, three ratios to 60mph with a 12.67 starter gear will be incredibly quick, even with a stout teener.
See, the teener is not gonna spin all the way to 60, like the 408. If it spins all the way thru first,this will be 38mph. But I think it will not spin that far with 295s. And I think,there is yet another option.
> A regular 5.9er.This engine makes a lot of torque. For a streeter that 12.67 starter is too deep, and the cruise rpm of 2582 is too high. So, a good compromise is 3.55s. With these,and still the GVOD, 65=2240. The starter gear is 10.97. 60 mph is a 2 gear romp ending at 6380 in first over. 32mph is 4360rpm in first gear/2700 in second;The downshift (4360) is just over peak torque, with most street cams.
> So, now, having the tranny figured out, it is no big thing to build a smaller engine to fit this business. I tell you for sure that 408 is gonna make well over 500 ft lbs of torque, which means you can stomp on it almost anywhere under 60 mph on street tires and spin. Do you need that? It will make driving aggressively, tricky on street-tires, on the street.
> I have a 360 that will spin 295s at 50mph in second(3.55x1.91) gear @4200rpm. There is nothing special about this engine. Do you need that?
> I'm guessing not, so again;why the 408.
> to hit those above targets, all you need is a small-cam 360/5.9er. Somewhere just over 380hp Ima thinking.

> In this same way, a combo could be worked out to use an automatic.
A smaller engine would allow a 904HD tranny, read cheap, as compared to what you will have to spend on a 408-capable tranny. And with a deep low, a smaller TC can be used. And all the support works can be lighter duty. Even the rear end could be an 8.25 instead of an 8.75. And the smaller engine might allow for smaller tires.
> On the street, it doesn't take nearly as much engine as one might think, to have a lot of fun. It's all in the combo.
> But if the 408 is what you have your heart set on,return,back to the top.