Teaching that judgment call

I just returned from a dual cross country, ferry flight. Basically a new student bought a plane which I went with him to finalize the purchase and fly it home while giving dual.
I actually like these trips, though can be tiring, and some parts stressful.
There may have been times student might have wondered if I'm teaching or going along. Sometimes I'm teaching by going along with your plan, to see how you deal with the problems as they occur.

We encountered weather, but not unexpectedly, just wasn't sure where might meet it and how bad it might be at that time. We had a planned airport, but was also watching airports along the route especially as started seeing clouds in the distance. We began a descent to get below as we were VFR but had picked up flight following even though our transponder had decided to not work for that leg. That began first problem really, By having the ATC work us, but sometimes losing our primary on their radar occasionally meant turning or such or position report to find us again, which then noticed the distant clouds not so distant but least scattered. We began the decent and then at a certain point we were getting uncomfortably close to the ground without escaping clouds, which I bailed and turned tail. Unfortunately clouds were gathering there too. It happens. None were stormy clouds at least. I turned back to a recent towered airfield, and asked for that ifr descent down. They pointed me first to a hole, which I wasn't fond of that plan, but student was already pointing one out. I looked and it was closing fast. I must mention no I do not like approaching ground blind without knowing the path I'm taking (i.e. the instrument approach procedure type). Yet it became a moment to teach why I have that fear safely (you cant hardly buy this training in the real stuff). We searched for one whole that closed then turned back and found another and stared down, By now student is letting me do the flying of course as this entails slowing the aircraft and maneuvering it and prepping for a landing etc. As we descended the hole closed yet I continued.... now that was in many cases a stupid thing to do, what's beneath the clouds, like towers, and what altitude above the ground will I be, and where is the airport and the traffic too?
I continued to drive home those thoughts. In this case I knew exactly where we were when lost visual as I was on the approach end of the runway but downwind end. My Garmin 396 shows the feathers of the runway, which at the time of finding that hole was in perfect alignment. (this rarely occurs so I took it). So nicely I broke through looking at the runway which then allowed me to shift to a downwind and setup for a landing. Being that was a towered field also meant they had traffic controlled for me, granted none there but they would managed if was. plus knowing the approach end of the runway was clear least there allowed me to demonstrate why shouldn't do this. This skill came more from years of hard IFR flying not dumb luck. I had to learn to become somewhat comfortable flying in the clouds, and face my fears but not let them prevent from flying the plane even when faced with doing exactly what I fear.
My student faced 3 more hours of IFR work that started mild and ended with stuff building faster than Stratus and my XM were updating while on another approach. I again flew that approach, wasn't hardly a passing approach for a checkride, but the weather building on the approach path was not a situation one probably plans for especially when you get the notice after in it (think embedded storms). now none were sever storms but enough to bump us about force me off the approach path at one point, and with me juggling everything from a handheld mike to plane and approach chart, I nearly put myself in an unusual attitude. I saw the turn I didn't intend which immediately stopped the turn, *granted part was from the turbulence of the embedded storm... dropped the mike and talked out loud for my student to talk to atc, I told him what to say while I flew and returned to course around the new storm, which atc now also saw and assumed as much. All finished well and smoothly and broke out much earlier than expected and dropped the ifr and landed.
Next lesson was just as fun to teach. It 4pm local sun will set in about 3 hours or so, and there is weather, and we are now wore out from such a rough flight plus previous long leg and no lunch. I began by asking what he wanted to do other than yes we both wanted to be home tonight, but I would not fly a unfamiliar plane at night over unknown territory and that was over 5 hours away, and worse with those 30-50 kt headwinds we have. so left with an option could fly to another airport just as friendly or better couple hours more or possibly stay. Student was quick to realize finding better might be futile search, plus still have that weather building in our path, and both hungry and tired.. but even so he hesitated to stay, but yet delayed leaving by finding a snack and looking a few minutes at weather and an extra trip to the bathroom. Finally decided to stay put start early tomorrow. We got a cab to the hotel then found a restaurant. It was after eating and now relaxing because we know are no longer in a any rush, that he really knew staying was the best decision.
Often we look long after given in to our decision and realize if was a good one or not. Have I ever bailed because of weather that didn't happen? yep but less often than not bailing when should have. Its that moment you relax knowing the decision is made that can see if was right or not, its hard to see when in the middle of that moment mixed with I really want to get there plus all other maybes you think of...so when you cant seem to get someone to not take the wrong choice or they are on the fence, they wont hardly feel the rightness till its made and minutes or even an hour passes. This is why funeral words get used or such and even a call to home saying hey I know you want us home now but its kind of worrisome weather and I'm really tired, and maybe even afraid I might do something wrong then not ever come home again... they tend to make that decision for you... even during holidays...