Great question and discussion!
I’d just quickly add, I have personally started with and still primarily rely on the ‘gestalt’ or ‘feel’ for various family, genera, and species ID of local plants I’m familiar with, but am coming around to using keys and local/county species guides/lists (like CalFlora) to at least rule out or narrow down more tricky IDs to the species level (whether mine or others’).
I think the original question had a really important consideration that I haven’t seen in the discussion yet (might have missed it), which is that there is some risk in not making higher-level IDs–or stretching your comfort zone a bit.
Leaving some observations at order or family level (don’t get me started on the many ‘Plantae’ IDs I’ve gotten) I believe can put an observation into limbo, since there’s 12 million observations for ‘Plantae’ between Jan 1 1920 (earliest date available)–Jan 1 2020 in Plantae, but nearly an order of magnitude (1.6-1.7 million) observations even for the species-rich orders and families Asterales + Asteraceae.
I assume some braver souls than I trawl Plantae for ID purposes, but that seems a monumental task!
On a side note, I’ve only recently gotten into subspecies/variety-level IDs, for which I almost currently always rely on dichotomous keys and species range (location) maps, and habitat/substrate to determine just what I’m looking at–here’s one example where I waffled around on a Cirsium occidentale species before coming to a subspecies ID through use of range and habitat maps with some help from @morganstickrod.
I’ve also started looking through some of my older observations, which can be somewhat embarrassing/humbling to see how little I knew just 2-3 years ago about the observations I was making at a species level!