A few thoughts:
If the cash delivery was pre-planned (before Wed PM)/a regular occurrence, and DW heard about it "through the grape vine", wouldn't it have been a lot easier to intercept the driver outside the house on the day of delivery, rather than take a whole family hostage and hold them overnight?
Is it possible that W1's employment was about to come to an end? If he didn't know SS would be killed, he had to know SS would discover the missing money, so he would certainly expect to be fired, if not prosecuted. Taking and texting the photo of the money is really hurting his credibility.
What's with the red bag AND manila envelope? Did SS tell him to bring them? As I've scoured SM searching for "clues", I've noticed a number of people posting photos of artfully arranged cash, often captioned with something like "Money, Power, Respect". If W1 was doing that, it would explain why the band was off one of the stacks. But why put half of it in the red bag? Why wouldn't he just lay it out on the seat of the car? Or photograph ALL of it? If you're looking to wow someone, wouldn't $40K be twice as impressive as $20K, even if you're just having fun and planning to put it all into a manila envelope to complete the delivery? I feel like we only know a few facts about this guy, but all of those point to someone immature and impulsive. I can't imagine there weren't other warning signs that would lead SS to worry about having him around his family.
W1 had a gazillion SM accounts to which he posted photos and video. I wouldn't be surprised if someone in the family came across one of these posts of the interiors of their cars and found it immature/unprofessional/possibly dangerous. W1 is the star of every "company"/video/SM post, so finding himself more pit crew/support person for a ten year-old than the center of attention, especially in the "racing community" could bother him. If he already knew he was about to be let go, it would make more sense for him to plan to rob the family, either alone or with someone else's help (DW). Yes, I know this is all conjecture! :blushing:
I think LE is waiting for co-conspirator(s) to lead them to/come back for something big. There's some reason the entourage was driving that rolling garage - it's just not the most convenient/unobtrusive vehicle for a drive down NY Avenue. Is it normal for a crime scene to remain active for as long as the SS house? I realize this is not a "normal" crime, but it seems like a long time to still have techs there and the street blocked off. FWIW, I'm not saying they were heading to the house with the truck. These two observations/presumptions are probably unrelated.