The Windsor is a great choice. The 409 I have is mega-reliable (147k so far and never been touched) and a hoss.
As far as trannies go, you can spend a bunch of money on a "built" one or take a chance with a toploader 4-speed. I've heard the Tremec is a sturdy box, and I'm THINKING about one . . . someday, but it's tough to beat a topper. They're bricks. You've got to WORK to break one, and, unless you're going to put some monster meats under your car, you'll probably spin the tires WAY before you load up your box.
There are some drag shops in Memphis that will sell you a cut niner with discs for less than a grand . . . last time I checked.
The big question is how often do you want to drag this puppy in relation to cruising. If you're going to hit the strip twice a weekend 35 weeks out of the year, then you'd better opt for all the pricey equipment.
If you're going to try it once or twice, feel good about the car, and then go hit Sonic for a few months, eh, a good toploader and a reasonable 9-inch should do you fine.
Mid 13's aren't THAT far out of sight with a stroked 351 . . . even a mild one.
Remember, though, if you want to go quick, you're probably going to tinker with the gears which can eat into your reliability (long term) and gas mileage. I run 3.00's, and I'm doing about 3k at 70mph. I do OKAY mileage, but it costs some cash to travel even with that high of a rear. I cringe at 4.11's or even 3.50's. Of course, with a 9 it's easy to change the rears out.
IF this is a daily driver, let me make a suggestion. Don't build a dedicated drag car. Build a ROAD car with enough engine to drag. Horsepower is nice, but a big motor WON'T save your life. Big brakes, QUALITY suspension, and some ultra-sticky Toyo tires WILL. Trust me on that one.
Oh, did I mention Toyo tires?
Good luck!
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