Well, people on the board here have different opinions on this subject. If you want mine opinion, I am wanting to do the same thing your doing now. I have an '00 auto. , with RV 275's and want an Edge Comp, but need to address the transmission first. In my situation, I am going to buy an aftermarket TC and VB because, I have put all of the 95,000 miles on my truck and have taken very special care of my transmission, serviced every 25-32K, just had normal wear according to the magnet in the pan, never experienced a shudder when towing, and 93K of the 95K on the truck has been bone stock. I just can't justify $3,500 for a new transmission when I can spend a lot less and it do the same job. I am not running twins or nothing, probably not thinking of having more then 400rwhp, so a VB and TC will do me in my opinion.
Now, another thing I have been thinking about and I am not really sure if it will hold is a B&M performance kit and also a TCI torque converter. The TCI is in the jegs book and it is better then stock from what I can see, but don't think it is better then the other ones like DTT, ATS, Suncoast, etc. , BUT maybe it might be good enough. They are only $375 in jegs. And the B&M kit is like $50, so for around $450-$475 shipped to your door, you will have a better then stock TC and a kit to up your line pressure. Is it worth it? I have no idea. Is it worth a try? I am still thinking on that question.
JD