Sean, can you get any repeatability at all?
I bought a 'ridgeless' years ago that the tamper would bottom out on. The stock Rancilio double basket isn't bad.
Try to remove some of the variables:
1. Revert back to stock double basket. See if you can get any repeatability in shots. 3 sour shots in a row, roughly same extraction time, or 3 bitter shots in a row. We're trying to take variables out of the equation.
2. Is your dosing routine the same each time? Tapping the portafilter can effect the density of grounds in the basket, and can add a surprising amount of time to the extraction. Try dosing with no manipulation of the grounds until you have a full basket. One key is how high the tamper is sitting after you tamp. It should be the same height each time.
3. If the tamper is bottoming out, you'll need to replace it. If you can afford it, I like the Reg Barber 58. There's quite a few good ones, and this thread
http://www.home-barista.com/knockbox/hb-roadshow-espresso-tamper-reviews-t1912.html shows the measurements of various models.
4. Tamping pressure - are you confident your tamping has approx the same pressure each time. Make sure that you're straight up and down, and the same pressure. Take a look at the tamper after and see if it's straight.
Run through the steps. If you're able to establish some consistency, even if it's bad, it's a place to start dialing things into the sweet spot.
Also, remember that the stock Rancilio, even with fastidious attention to temperature surfing is still going to deliver somewhat inconsistent results. But work on getting consistent extraction times, and then you refine the other parts of your approach.