Picking gears

For me highway is no big deal
I live just outside of Toronto, even if I do highway it into T.O. its for 10-15 mins max.
Now to go to the drag park from here is a different story it's a couple of hours away.

I'm torn with going straight to 4.30 and maybe go overdrive over winter or compromise with 3.55/3.73/3.91.

I would like to do some traveling with the car but could always swap in 2.96 before hand if I don't go O.D.
Been there done that;not going back,lol

I got a compromise for you, that worked pretty good for me; namely trap in third gear.
But first run the 2.96s to get an MPH number. Then gear it to trap in third gear. Then get yourself a 3.09 low to blast off with. Then move your power curve to the middle of the trap, and you are done.
So if 4.30s were the right gear,the math says 4.30 x 1.00top gear= 4.30final drive, and 4.30/1.39 third gear =3.09 gears to trap in third. The final drive ratio is the same 3.09 x 1.39=4.295
Your required gear is between availables, (2.96 and 3.23s), so I would try the larger one to help with the 60ft. Now 3.23 x 3.09=9.98 starter gear. This would be about equivalent to 2.66low x 3.73 rear=9.92. Now you have both ends covered, allbeit with just 3 gears.
And you still get to cruise to the distant track at 65=2700ish, with those 3.23s. Problem solved.
Now the above was based on the 4.30s being the optimum gear. Your first run with the 2.96s will sort that right out. This is a tuning opportunity you shouldn't miss,IMO.
Furthermore the 3.23s will not get you low-ET cuz you are missing a gear. Which has decreased your average power put down during the run, as the engine is forced to spend more time in each gear. I call this no big deal, cuz the option is to spend a wheelbarrow full of money, chasing low-ET. I'm happy just knowing my car could be faster if I was rich. And on the street, it matters not a whoot!
Oh chit, it's a 727/2800 :( Sorry about that

Well in that case do what I did; put a 4 gear in it,lol.
But seriously;
Trapping in second gear with an automatic and a small engine is like watching grass grow; who does that?Well you're a bit ahead with the 360/380
The only cheating you can do is to race with short tires and cruise with tall tires. But there is barely one final drive ratio equivalency to be gained. Been there done that, ain't going back.