I'm barely going to be able to afford to race a 409 after wanting to swap one in place of my 427 for years.....certainly no way I could afford to with a stick behind it....so I'm going to stay with my th400 and 8" convertor.
I believe a manual would be more fun and more appropriate for the car, but it takes a lot of money, time, money, knowledge, money, clutch tuning, money to get one to live and work right. Did I mention money? LOL I've got less than $1500 in my trans and convertor and have been served well for years by them. That much would get you a decent Muncie or T10 (which won't last very long with a lot of power and good tires) and a good clutch / shifter combo. I'm betting you'd be looking at replacing the clutch about every year if you run it much. A Jericho would last a whole lot better, but that is another couple grand I think.
I do have two Muncie 4 speeds complete with everything to install them, but I don't like the idea of trashing them both within the first couple years of racing.....so they will stay for street cars.