But....am I ramped up or not.....?

The Workers->Shift Graph will currently show that clearly.
The light red area is the 5Nd, so if you were mining since the beginning of that area (or before) then you are now fully ramped up.
Again, as a reminder to all, the 5Nd 'ramp' isn't a time interval, it's an amount of hashes - specifically 5 times the network difficulty.
Since the pool hash rate changes around quite a bit, the 'time' for the 5Nd is quite varying

I'm fully ramped up according to the Workers>Shift Graph; however, on the Workers>Shifts page,
there are 86 shifts between the
bold red line and the 1/22 block where I'm not seeing a reward.
How/when will I get rewarded for that time period? Thanks in advance for the explanation.
When a block is found. The reward process counts back shifts until the total share difficulty included is 5Nd. So the red line is showing you were the 5Nd point is. Rewards are averaged between the redline and finding the block.