note that I changed the PID when I turned the machine on cold... and let it sit there warming up for about 45 minutes.... I didn't change the PID after the machine was already wamred up and only waited 15ish min... Though I would have guessed that the grouphead would get to temp within 20 in that scenario

Typically my espresso over the time I've had this machine has been lacking body, and rarely would I get a color in the cup that was as dark as typically seen elsewhere. Sometimes bitter, but mostly just lacking flavor, and generally not so great (tho still better than starbucks).
I drink mostly latte's... Largely due to this, but I also enjoy them a lot, so it hasn't been the monster concern it should be.
I've had all sorts of extraction issues for probably my entire barista'ing life. I recently received my RB "American Curve", custom engraved tamper. The huge difference there isn't really the curve (or engraving). Its the fact that the topline of the business end of the tamper aligns VERY well with the top of my bascket - Therefore it is extremely easy to see if you've tamped level.
This has fixed a lot of my extraction issues, and therefore peaked my interest again in getting my espresso going in the right direction. With all of the extraction issues its pretty useless to try and fix other things (IMO). And trust me, I've tried to fix my extraction issues to no avail... Apparently TRYING to tamp level, at least for me, without a good reference, is nearly impossible.
This last latte I just pulled was a tad slow, so I've adjusted the grind just a tad and left the machine on for "more research"
