I can't help much with details of the sequence, but the 6900 Series basically followed the changes in the full size 5900 Series. I was a big fan of 3rd Generation S&W Semi-auto pistols from the beginning... and still am. I do know the squared trigger guard came first... a carryover from S&W 2nd generation pistols.
The 5904/06, which begin production in 1989 had the pronounced "Finger step contoured serrated trigger guard" resembling the Beretta 92 on the older models. S&W changed that to the rounded front trigger guard with serrations to reduce production costs, but I don't know exactly which year they finalized that change.
Likewise the 6904/06, which began production in 1989, first had the very pronounced squared front trigger guard with serrations. And like the 5904/06 S&W began producing models with the round trigger guard with serrations at a later time.
The squared off trigger guard with the hook at the bottom were made at least from 1989 to 1991. The first rounded trigger guard I saw on a 3rd Generation S&W was on a 1992 5904, which was the duty sidearm of an Illinois State Police friend of mine. I don't know if the 6904/06 changed to the rounded trigger guard in 1992 or not. I wasn't very familiar with them at the time.
I have an early production model 915, which at the time was introduced as a "Budget" 5904. The 915 (1992 - 1995) always had the rounded trigger guard. I put Novak sights on it. At this point it's barely distinguishable from the later production 5904. They both fetch about the same price used on Gunbroker and other auction sites. I actually prefer the 915. Its a bit lighter and I don't need the ambidextrous safety of the 5904. I've handled 5904s with the squared trigger guard and I like those as well.
genitron.com shows only 2 variations of the 6904/06. Variant-1 with the trigger guard that has the squared off front, and Variant-2 with the rounded front trigger guard. But they could be wrong. There could be a third if you've seen it. There's a lot of conflicting info on the web. It's hard to find a definitive answer about some details. Smith & Wesson did quite a bit of custom work and experimentation with the 3rd Generation autos.
https://www.genitron.com/Handgun/Smith-Wesson/Pistol/6904/9-mm/Variant-1
https://www.genitron.com/Handgun/Smith-Wesson/Pistol/6904/9-mm/Variant-2