Upgrading to Aspire 9.5 will answer your questions about tapered flutes. I don't believe really old versions like you have would be capable of doing it. To create the flutes, I first used a bottom cleaning bit large enough to cover the width of the area I needed to taper, then used a fluting bit. The bottom cleaning bit running a fluting tool path is the key there. In Aspire 9.5 the preview is amazingly accurate. You'll know you're in the right ballpark once you see it emerge in the preview. Unfortunately, the preview isn't perfect and you'll have to experiment with the actual bits to get everything right. I use cheap 4x4's for experiments. They work great and are plentiful.
ShopBot Details:
2013 PRS 96x60x12 (Centroid upgrade)
4hp Spindle
12" indexer
Aspire
Rhino
Fusion 360
Ferrari 360
Prusa MK3S+
Prusa XL multi-tool