Wow, Black Bear is still in business? I've had personal experience fixing his tunes, but that was 10 years ago. I had to re-do a few trucks with his tunes that I knew were doomed if they didn't get fixed. Way too much ignition timing and whacked out fueling. Trans calibrations were pretty harsh too, simply took out a pile of TM to make the shifts feel firmer.
That being said, I put the 10 years ago part in bold because if he's still in business, he must have figured out a thing or two! I would give him the benefit of doubt and not rely on what his tunes were like a decade ago. The truck engines haven't changed too much until the DI versions, if he figured out how to make his tunes work it's not like you'd be asking him to tune something new and different. Even the trans TM part, that was fairly common practice years ago, most tuners just wanted to eliminate all torque management. That's the absolute WRONG way to tune. Sure, you can make a tune "feel" good and strong, but it won't last. Dropping engine torque during shifts is a good, I'll say even wonderful thing to do. lol. If done correctly, it makes for nice quick shifts that don't hurt the trans or driveline even behind huge hp engines.
If your truck is a GMT900 or earlier, I'd say have him do it if his feedback looks ok. The DI engines are trickier, there's still a lot that these "tuners" don't know about them. I have no idea if he's figured them out, I haven't been hanging out in the HPT forum for awhile and haven't done tuning for any private parties for awhile either.
Obviously the other way you can go is to just do it yourself, but that takes a lot of learning and logging. And time, you need to take careful and slow steps. BTW, whatever tune you put in your truck, I would STRONGLY SUGGEST that you learn how and what to log and then log, log, log. Seriously. When I tune a vehicle, I log it every single time I drive it. If you don't log, you're tuning blind and that's when bad things happen.
Hope that helps!