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Right on both counts - no dispute here.

What am I asking more specifically is:

What criteria do you use to put your trust in Trad clerics on the subject of doubtful baptisms i.e., their method of how they come to determine if someone's baptism is valid or not - this would include men who come to their seminaries from the Novus Ordo or other Protestant sects, and either being conditionally baptized or not. It seems to me that because we do not have recourse to the Holy Office, so it is every man for himself, based on his preference, gut-feeling, powers of deduction, etc. So, we choose to put our trust in different groups/people - what is the criteria you use to do that?

An additional factor to consider:

Say your priest was a Novus Ordo convert, or Protestant convert who was baptized in that sect but never received conditional baptism. Without having recourse to decisions from Rome, how can we be morally certain they are even baptized due to all of the fallout from the Novus Ordo fiddling with the rite of baptism and also from the general principle that many Protestant converts were conditionally baptized when entered the Church based on "reasonable doubt". No baptism = no priests. To approach doubtful Sacraments is grave matter and forbidden.

So maybe someone would answer, "I choose to align myself with the way bishop so-and-so does things because I think he is smart"., Or "I follow the principles of our organization, etc. Or maybe people never think about it and just go the Sacraments assuming their priest is validly baptized. But is such an assumption prudent during this time? That is more what I am driving at. What are your thoughts?

Maybe, like I said above - your priest is undoubtably baptized/raised in Tradition and so were you. That is a HUGE grace and then the question probably never came up to your mind.

In general there are no conditional baptisms for converts from the Novus Ordo, but in our case, the priest did perform the exorcisms that are no longer done

But, yes, I would recommend conditional Baptism / Confirmation and then Ordination for any priest baptized in the Novus Ordo, and just Baptism / Confirmation for anyone else baptized in the NO.  I've stated that here.

Some Trad groups do an "investigation" IF you were baptized between certain years (I actually believe they have it flipped in terms of the years they focus on), whereas others assume validity.

I've never understood this ... at all.  They're so worried about some kind of "sacrilege" against the Sacrament, but that's the entire point of CONDITIONAL Sacraments, where it it was already validly administered, it's not done again.  So there's absolutely NO danger of sacrilege when it's administered conditonally.

Now, you can't just willy-nilly rebaptized everybody based on "what if my priest got the words wrong?" ... since that would just make the Church ridiculous (subjecting everyone to the same standards of proof that Bishop Kelly made up about the +Thuch bishops) and making a mockery of the Church.

But due to the prevailing attitude in the NO where "ad libbing" stuff is OK (this is a widespread mentality among them that I've run into on a regular basis), I would consider it perfectly reasonable to conditionally baptize everyone baptized in the NO.  In addition, I would supplement the conditional Baptism with the additional Traditional Rites, just as you would if someone received emergency Baptism without the solemnity.

I've never understood this IMO absurdly-over-cautious attitude about some kind of possible sacrilege against the Sacrament ... which can't happen if you use the conditional form.  I believe that it's perfectly reasonable ... and highly recommended to engage in this practice, unless you actually have positive indicators that the NO one was valid.