Have dedicated Thumb drive in radio case containing... "Can be also used to offload logs at site".
All N1MM updates and Documentation.
All N1MM files pertinent to setup for contest...NYQP - Field Day..etc...
NYQP PDF of Counties and NYQP contest rules, NYQP contest Setup for N1MM (Ken Bosai).
PDFs and all files for Icom 7300.
Driver files for Radio. I.E. USB Drivers for Icom 7300.
Ham Radio Deluxe optional.
WSJT-X files (Setup, updates, etc...).
Text files of Setup strings for Icom-7300 (Voice File Macros and etc...).
Manuals for all equip in PDF on usb drive.

Cables in appropriate Pelecan Case to support Radio or accessory, not spread around.

Better labeling.
List of Contents for Case.

Bring extra Generator and Parallel Kit.
Bring non electric Coffee Maker - no generator load. (screaming meemie)
Bring Electric flannels ?