Planning Trip KHPN to KSAF

I don't think I'd try in in one day with the chance you'll end up at
SFE in the dark. An early departure out of OJC will hopefully put you
in the SFE area before the winds come up and you'll have lots of
daylight to see what is around you. Always good chance that you'll be
bucking headwinds and delay your arrivals westbound.
Keep it uppermost in your mind how to figure the DA and how it will
affect your aircraft performance. Most pilots just don't really grasp
it until they see how the DA affects their particular flight with take
offs above 10,000 DA.
I don't see anything particularly unusual about the flight and the fact
that you seem to be planning it well indicates you will find most
problem areas anyway! Lots of tall hills around the area and
spectacular scenery. I often went there for ski trips while flying a
corporate Merlin.
Have fun and enjoy yourself.