Thanks for the opinions and compliments so far guys, appreciate it.
ShutterTonight wrote in post #17389783
I would lose the heavy vignetting
Gart wrote in post #17389925
Brandon,
I prefer the color more than the B+W's.
Vignette, if you purposely did this, doesn't bother me but a little tighter crop (especially on your son) to lose some of the dead space would work.
If I had to find something that I would pass to learn from, it would be: The shadow from your wife's nose crosses her lip. The shadow from your son's fades away at that point (corner of lip). Although your shot is not done in true Rembrandt style, the shadow shouldn't touch the lip.
These are good shots. You and your family should be pleased with the results.
Gart
Yes, the Vignette was done on purpose (playing with Radial filter in LR). I realize not everyone likes vignette/heavy vignette but personally I liked it better than without. It was one of the last things I did to the image.
Good info on the shadows Gart, thank you. I'll try and keep a better eye on this next time. I know there are all sorts of "styles" but I don't know yet how to recognize or setup for each. I was just going for something that looked "ok" in my limited testing. I really should be spending more time on the reading part of learning, but it's so much more fun to "do" 
I went pretty cheap for the setup because this isn't something that I think I am going to do all too often, but it was still something I wanted to learn to do. Honestly, I'd prefer to be outside hiking and aiming my camera at landscapes, but it's winter, the weather is crappy and I'm lazy.. so anyways...
I'm using a Speedlite 430 EX (I've had for a number of years) and then I picked up the following:
Yongnuo RF-C603
(wireless shutter / flash trigger) - I chose these because they were pretty cheap, had good enough reviews, plus I could buy more and link together, and I liked that they doubled as radio shutter release. I figured if I ever got into this more and needed a better system, at least I'd have these as RF remote shutter that is wayyyy more flexible than my cheap IR one.
Westcott 43-inch umbrella
Cowboy Studio light stand
Cowboy Studio umbrella stand mount bracket
Yes, I am reading The Strobist - Lighting 101

Griffey24 wrote in post #17389855
What did you change from your first "failure", to this time around?
It was the first of a couple trial and error testing runs and really came down to the sync between flash and camera. I honestly still don't know where/why I am being limited, but after some more reading and more testing it looks like I'd limited to 1/160 for everything to sync up right. Once I figured this out, then I was able to concentrate more on where to position the umbrella, power of the speedlite, etc.
Question for those of you that specified you preferred the color versions - is it my conversion that you don't like, or just in general for this type of shot you prefer color? Curious, thanks!