I think we >90% agree, but I think for a couple of your rhetorical questions I come to different answers, and at the end a couple of situations which you mention seem absurd seem reasonable to me. Hope you don’t feel needled by the way my brain zooms in on disagreement or potential disagreement
, I really do feel like we are generally very aligned.
To me - Absolutely yes. I think it’s special to get to know when plants have that history, and I think we need to keep sharing that history when we talk about those plants.
Presumably because those are wild (self-propagated). For a plant in it’s natural range which is capable of completing it’s lifecycle in a place - I would assume it’s wild unless we have access to a record otherwise. This assumption is a part of why I view an accurate record as being something quite precious and important - if we don’t share the knowledge with others as best we can, they might never be able to confidently know.
I think it depends on why it is burnt, but whilst the answer could be yes, it is an act of cultivation, I would say that it does not cultivate any individual plant. So for the purposes of the iNat distinction; I would say the plant coming up in the cultivated burnt area is wild (you can maybe see why I sometimes use “self-propagated” as a synonym of wild.) I think fire is a good grey-area to talk about, but I’m wary that we might hit some linguistic/cultural confusion. I don’t know anything about fire use in North America. If we were talking about burning a grassy system closer to my home (Australia), I’d say that we are probably going to struggle with applying dichotomous labels like wild/cultivated to the effects of a cultural practice like burning in Australia.
Well, now I’m more than curious! 
Perhaps unrelated, but might interest you: I read a paper recently that found a couple of the apparently “locally sourced seed stock” were not local https://www.nature.com/articles/s41598-023-33720-z . Given the genetic biodiversity loss that often occurs when people plant non-local stock of local species, I’m hopeful that plantings of long-lived trees for “restoration” will eventually have their genetics checked wholesale. I don’t think it is true that restorations only stay cultivated so long as someone remembers, but I do think it’s true that openly sharing the knowledge is the cheapest way to find out.
I do think that every individual plant that was cultivated, should be marked as cultivated, and I think self-propagated is not cultivated. So I’d say yes? I don’t think this is unreasonable, but maybe some of our definitions aren’t lined up?
Our definition of a “weed” might differ (I would normally define this as a plant that is growing where it isn’t wanted, and I guess you mean introduced naturalised plants?). I’m a bit saddened to contemplate that there may be no native plants left which are wild left in Chicago. Perhaps saddened to the point of disbelief. If there truly are no self-propagating native species left in Chicago, then yes, I think the only research grade plants in that area should be weeds. (Currently, but as I said before; I also think the system should be changed so that clearly labelled cultivated plants can become research grade).
Ideally, I would hope that suspected plantings are checked for this by the observer rather than the identifier. There aren’t good records of these kinds of things in Australia, so I find myself looking up historical aerial imagery to make my best guesses. I would love it if we had records like what you are mentioning.
Even better might be if the people associated with the original planting program documented what they had installed on iNat themselves (that way the knowledge that something was planted in a place is associated with the location, rather than that knowledge being kept in the records of various institutions outside of the dataset). Plus, this way people could independently review how how things are growing, and what plantings have survived.
Cool thankyou! I’ve joined that discussion (added a big comment which may interest you) and added a vote. 