Jumped into this late as I just saw it...but
did you do the flight?

If so I bet it was alot less eventful than you guessed it'd be. Is this an
owned or rented C182? Rented I'd have a few more reservations, owned and
well known - not that many.

This night/single engine/mountain flight stuff is always a hot topic amongst
a couple pilot friends of mine. Perhaps history and training has something
to do with it (they were trained where mountains are no higher than 2k, I
was trained from the Continental Divide and west). As far as the 2 out of 3
rule, if those 2 are single engine and mountains, is that a no-go factor? I
guess I'd never fly then. This IS a C182 you're talking about, right? They
go considerably higher than 4k or even 8 or 10k feet.

What is the comfort level then? Gliding distance to an airport? 3-4k above
terrain? Does that number change based on winds or cloud coverage? I'll
take clear night VFR over Gorman than solid IMC down there in the day.
Personally I'd take the Gorman routing over the coast (IMC) or Tehachapi
Pass (strong winds), but have done each several times. Now I have to deal
with passes no lower than 10k if I want to go west, they arent to be feared,
just respected.

Just for grins I fired up Anywhere Map Flight Planner, it's the one with the
"Cones of Safety" that put circles around airports. It is based on your
altitude and the glide performance you plug in. It doesn't account for
winds. Over GMN at 8,500 you'd be still within glide range of CL96, and
over GRAPE intersection within gliding distance of 7CA2. There is a gap in
between though. Bump that up to 10,500 and that gap is gone. Use those
numbers as you will, no guarantees you'd make those airfields, may have to
do everything RIGHT to make it, but it's not like flying through the Andes.

I guess what I'm trying to say is, personally, I don't make my go no-go
decisions based on personal opinions to the extent I sit and not go at all.
Typical scenario for me is to get in the air, climb up, and make my decision
before the point of no return. Often times that's at 12,500 approaching the
Continental Divide westbound. The decision has to be made to climb,
continue forward, take notice of up/downdrafts and turbulence, visibility on
both sides of the pass, etc. This is without the benefit of a international
airport width continuous runway (I-5) below. Foolish to make this flight?
I think not. The fact you ask it though... if you're not confident in your
decision making skills or the airplane, then you should have doubts.

Go get a mountain checkout, and read the book "Mountain Flying Bible" by
Sparky Imeson. Just for fun fly it with FS2004, it'll give you some idea
what it'd look like with varying altitudes, weather, and darkness. Cut the
engine while you're at it. Simple rules don't apply to all decisions. As
far as IFR or VFR - fly VFR with flight following, that way you can pick
your route and fly directly over airports as you see fit. The airways don't
always do this for you.
And Greg, that "Bakersfield, Santa Barbara and back to Brackett/Pomona"
mustve been popular with instructors, mine assigned that one to me, too.
In a Traumahawk no less.
Chris