While I guess anything is possible, and yes, you should have thought through the dive plan before doing a bounce dive to retrieve the dropped weights (to decide, for example, the maximum depth you would go for your search, the maximum time you would spend on the search, whether you had sufficient air for the dive, how the dive would impact your subsequent dives on the same day, etc.), in fact, if you had made a plan, and carried it out, you would have figured out you could do this dive with very little risk other than some catastrophic failure.
If you had decided, for example, that you would dive to a maximum depth of 35 meters, and in doing a dive plan you found that your NDL was 13 minutes, then that would have been the basis of your planning. On top of that, you'd need to calculate your air reserves, but as an instructor, I imagine that your RMV is pretty good. Mine is about 12 litres a minute on average, so at a depth of 4.5 ata, my tank would last me about 40 minutes; I should have plenty of air for a 13 minute bounce dive. As long as I had a spare tank on the boat to switch out and my AOW training dive was going to be something not too deep (like navigation), I might have gone down for the belt/weights.
Now as for considering a catastrophic loss of all your breathing gas at depth and not having a buddy to provide a redundant air supply, yeah, it could have happened. The chance of it happening would seem to be rather small, but still.... If you think you are going to be in a position to have to do some solo dives like this in the future, I would recommend that you find out about self-sufficiency in diving. There are courses you can take, or you can get some mentoring from somebody who is meticulous about planning solo dives.
So from this incident you can perhaps learn that
1) you need to plan your dives, even bounce dives like the one you did, so that you don't think about a bunch of "what if's" after the fact ("what if" thinking should be done beforehand with the aim of preventing mishaps)
2) you need to have spare equipment with you on all dive outings, including equipment (e.g., a stage tank) for the possibility of having to do a solo dive when you've got no DM with you to help out.