So I sat down with my CFI this morning and proposed my plan. He seems to think that I won't have a problem at all with this flight. In terms of executing my circling of the airport, I'll just extend my upwind a bit to gain some altitude before turning to my crosswind. There's nothing until ten nm north of the airport so this shouldn't be an issue. All of my turns at this point will be standard rate to hedge against disorientation. I'll have the KJZP CTAF already tuned into com 2 so once practical, I'll flip the lights on via that. I really don't think I'll have any major issues with pilotage at this point. There are two major stepping stones (KJZP and KCNI) that I can use--both of which are along a highway and next to a small town. And by the time I reach my 3500 MSL and exit the pattern, I should be able to pick up the KPDK VOR, which will take me straight over these airports and through the gap in the terrain. Of course I'll be getting flight following as soon as practical as well.
My CFI and I had a discussion about disorientation this morning and we both agreed that on previous night flights I didn't suffer from it; however, he made it clear that if I do start to feel it onset to focus on my instruments and to trust them. This is something I've never felt uncomfortable doing.
For a system failure I have a few backups. Obviously pilotage is my first resource, a VOR is my second, and the GPS is my third. I'll probably be relying on a mix of the 3 throughout the flight though. If the gyros go out at night, well thats just bad luck. But I'm confident I could still fly her as long as I stay calm. If the power plant fails on the upwind leg, thats just really bad luck; however, in the event of a power plant failure, I will have already scouted out the terrain on my inbound flight to determine the most appropriate place to try to put it down.
Between my plan to get altitude so that terrain can be avoided and airports are within gliding distance, 3 methods of navigating, weather that is looking great, a decent moon, and a commitment to focus on the instruments in the event of spatial disorientation, I'm feeling pretty confident about this one.
Obviously, like most flying, you are challenged some days but thats how you get better. I have a lot of trust in my instructor and he honestly looked at me like I was making a mountain out of a molehill. But he was still more than willing to address all my concerns, voice his own concerns, and provide advice. So as long as the weather looks good tomorrow, I think its going to be a go decision for me.