So at the beginning of August, I'm flying a 172SP 800 nm. from KBED (Bedford, MA) to KMKE (Milwaukee, WI) to pick up a family member and take them back to the east coast. My preliminary route out is:

KBED-KBFD (break/fuel)-KGWB (break/fuel)-KGYY (no fuel, just for routing purposes)-KMKE via the VFR route along the Chicago coast to the north.
The route back to Bedford looks like this:

KMKE-KGYY (again just for routing and flying VFR down the coast)-KPCW (break/fuel)- KBGM (break/fuel)-KBED

I was hoping to hear from some pilots with more experience flying long cross-country flights in single recips like this. Any advice for preparation, planning, etc.? Things to consider and common mistakes?
Thanks in advance for your responses.