Thanks, you have come the closest to answering my original question - though you didn't fully answer it either.
You seem to think the above guide is "decent", I see that it was lifted from a guide printed by the Franciscan Press in 1995 - I immediately think the 1983 "new-code of Canon Law". Personally, I would only use it for Firestarter. Vatican II stopped doing many conditional Baptisms due to the new ecuмenical spirit. The list you sent, states validity is presumed when one is coming from those sects - so ecuмenical of them! This way of dealing with converts is false. Prior to VII, the Church took baptism most seriously and anyone coming from a false sect would need to have the validity of their baptism confirmed beyond even reasonable doubt i.e. morally certain.
I think the list is just based on a high-level view of whether those groups tend to use a valid form and have a theological view of the nature of the Sacrament that doesn't invalidate. It does not speak to whether any of those groups tend to have a loosey-goosey, non-formal, approach to their rites, where any "minister" can just do whatever he wants. And that's actually most of them.
To have a strict ritual to which all the ministers (aka priests) must adhere (or are supposed to adhere) and where there's no mentality where it's OK to make up whatever you want ... that mentality tends to be limited to the Eastern Orthodox (and for our purposes, since the question is about Novus Ordo, the Eastern Catholics).
Such rigorous adherence to a fixed ritual is VERY MUCH CONTRARY to the Prot mentality, and there's widespread adaptation ... and actually it's precisely what you're referring to in the Novus Ordo, where that attitude has become very prevalent among them as well.
So, IMO, unless someone's coming over from Eastern Orthodox, or an Eastern Catholic Rite ... I would say a conditional Baptism is warranted and even advised. I heard once from some older priests that in fact it was common practice that if you came from some Prot denomination, they would conditionally baptize you as a matter of course (for this reason). There was never this attitude (that seems to be prevalent among the Traditional clergy) where they felt they must to a case-by-case investigation ... almost like one a marriage tribunal would do when researching an annulment.
What's being condemned by Trent is the scenario where someone wants to become Catholic and you just baptize them without making any inquiry, where they might tell you that they were baptized Eastern Orthodox or something obviously valid, or perhaps even Catholic when they were infants, but then at some point they left the Church, etc.
Depending on which denomination you came over from, one could make a general judgment (oh, Baptist? ... let's conditionally baptize you. oh, one of the strict Lutheran groups? ... not needed, etc.). It suffices to make a judgment based on a generalization based on group without a case-by-case in-depth investigation. Nobody has the time for that, and in 90% of the cases you won't get sufficient information to make a judgment anyway.
There are extremes on both sides, with a willy-nilly conditionally baptize anyone who comes to you with no questions asked even if they just have negative doubt on the one side, and sinful unless you can positively establish positive doubt in each specific case on the other side.
As long as you're making prudent judgment based on asking questions, that suffices to not cause injury to the Sacrament, and there's no risk of actual sacrilege due to it being conditional. What Trent was trying to avoid was guys going around baptizing everyone (including those baptized Catholic) "just in case", say, the priest did it wrong (negative doubt).