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Looking for some critique and suggestions on this before I move forward with it. I can see the asymmetry in the cheeks in the 3rd pic and it looks like the shank tapers towards the bowl. I also plan on bending the stem. Thanks in advance.

Is the bottom line showing me that I am not straight or that I should have had the shank at a slightly lower angle?

That's just to show the "elbow" between the shank and stem. Something wonky is happening in that area. There are too many parts involved to be sure from the pics, and how to avoid introducing The Wonk next time depends on what steps you took, and their sequence.

Ohhh gotcha...is using a bastard file with long flat strokes the best way to fix A Wonk or is it kinda like a kiss of death?

At this point I would bend the stem and continue to shape both shank and stem saddle accordingly. (Maybe touch a smidge of blade or the bowl/shank junction if necessary, as well.)

Shoot for unbroken, continuous flowing lines from every viewing angle.

I don't know if you are going to be able to correct the asymmetry/angle of that stem shank junction. It looks like you have a Delrin tenon and not a lot of room to work with on the bottom.
When I work on a round stem shank junction, I have found that rotating the stem 180 and 90 degrees periodically shows me where I am deviating from round, and it also shows if I am developing an angle from my centerline. This has to be done frequently or you will end up with a very slender shank/stem.
DocAitch
Also, on that assymetry of the cheeks, a contour gauge (device with multiple pins which is pressed against the contour) the pins take on the contour and this can be compared side to side. This helps to suggest exactly where material needs to come off. These are available in Home Depot for ~$8. If this isn't clear, I can PM a photo.