Light Tow in 65hp DD or 80hp Performance Tune?

[Powerstroke2000]

I'm new here, and thought I would ask my questions here, rather than bother Bill with them at this time.

I've got a '95 Ford Powerstroke, and have ran a TS Performance 4 position chip now for about 6 - 8 years, and I'm thinking I might like to have some changes made. I just had my pro-built tranny with the HD Tugger kit and Precision triple disk billet torque convertor maintained, and they also put a new solenoid in, so I'd now like to get a chip to get my shift strategies to work in unison with the power needed for the task at hand.
I've got the Tymar intake, full gauges, IDM mod, Mini-Me injectors, 5" exhaust and the above mentioned TS chip with 2 custom programs I like, albeit tranny shift mods are needed.

Now, my question is... can Bill reburn my current TS chip with his own programs (or work with and improve what is already there) thus staying with my current 4 positions, or spend the $$ and go to a different chipset with different programming?

I'm seeing chips with generic TS programs (6 positions) for reasonable prices, but after having custom tunes for several years making me wonder if it would be money well spent?

I should mention I'm quite happy with my current rear wheel HP output currently at 395 HP on the dyno, so being in the 400 range or just over is about perfect for my uses. I've built my truck for towing purposes mainly, and I drive by my pyrometer anyway, but I'm still running with my stock turbo, which I know is holding me back on lowering my EGT's at the moment. I'm thinking of going with a D66 turbo upgrade soon, and one day may change to an aftermarket fuel system, but hoping it won't be needed.
At the moment my higher tunes can truly churn out the "smoke" as well, which I'm hoping I can attain less with both "tunes" and a "turbo" upgrade.

Thanks in advance...