Thanks for the input here. Extremely helpful. I will 100% be attending the events in person. I've used the facilitator in the past for a SS grading and they've been total pros. I've looked into the insurance aspect and looks like I'll be covered for the full value every step along the way.
I'll probably skip out on the pressing since it would cost an additional 4% of the FMV and would likely not result in a grade bump or material improvement in the comic itself (while coming with the risk of damage). As it is, obtaining a signature will likely cost around $400 just for the submission (not including the fee for cracking the slab, shipping, the actual cost of the signature, etc.)
As with any high value item, as I'm sure you can understand, having it out of one's personal collection can be a bit nerve wracking.