I certainly wouldn't have wanted to put it down.
Not terribly friendly terrain.
I am, much like you seem to be, pretty conservative in my flying.
I am reluctant to cross water or broad forested areas.
So I try to pick 'oases' where I might be able to put down and move between them.
When I could see a bad stretch coming up, I'd add a couple hundred feet of altitude to increase my margin.
That said, I wasn't overly concerned about the terrain.
Fuel, yes. Cloud cover, yes. Head winds, yes.
I enjoyed it and would encourage you to give it a try once you've built confidence in your new motor.
A couple of things I'd do differently next time.
Fuel capacity obviously.
A better briefing on what we would do as a group if someone had a forced landing. Depending on pilot health, what exactly would we do?
A second bird with GPS capability. It occurred to me on the flight back that if Art (midget) had to set down, I'd be in a world of hurt - both pinpointing his location and finding the closest airport or safe spot to land.