@DriedupGoliath said:

I'd say Help on the Way> Slipknot> Franklin's Tower=Mike's Song> I Am Hydrogen> Weekapaug Groove

and

Sample in a Jar=Touch of Grey
Lifeboy=Black Peter
Slave to the Traffic Light=Morning Dew

Good call on the Slave=Dew pairing....That works nicely. I also like the Lifeboy=Peter pairing very much, more than the Ocelot=Peter that I came up with.
Not sure on the Jar=Grey one though.....think I'll stick with Backwards Down the # Line because it's very upbeat, and has a reflective "through the years" message.

I had Mike's Groove=China Cat/Rider because Mike's is a trifecta that has been in existence since Phish's early days and is always a crowd favorite, just like China Cat/Rider, which the Dead starting playing in early '70. However, Help/Slip/Franklin's is a true trifecta, like Mike's Groove, so you certainly can go there.
Another point in my imaginary game would be that China Cat/Rider was played far more frequently than Help/Slip/Franklin's, therefore is more comparable to Mike's Groove.

Either way, I need to get a life, don't I? This is way too much fun.