Don’t know my own rarest observation, but I can tell you my rarest id of someone else’s observation. It was just a couple of days ago: Velvetworms.
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I was thrilled to find the Pinnacles Shoulderband Snail. Some shells have occasionally been found in the park, but I believe mine was the first photo of a living individual and possibly the first living one seen (knowingly), since the original species description was based solely on the shell in 1936.
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I may have a taxon for that. Its a Gracillaridae spp. whose host plant is Mussaenda pubescens. I had discussed these observations in a relevant facebook page and was informed no records of that genus (Phyllocnistis) on that host plant (at least in the World Catalogue of Gracillariidae) so its highly possible its an undescribed species.
That being said, I wouldn’t say its rare (at least within Hong Kong) since M. pubescens is pretty widespread and I do on occassion see leaf mines on their leaves.
https://www.inaturalist.org/observations/52666793
https://www.inaturalist.org/observations/53252371
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It isn’t exactly rare but there are only 36 observations on iNaturalist of this coral and it is vulnerable https://inaturalist.nz/observations/40681170
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mechanically, is there an easy-ish way to find this sort of thing? Or do you just have to view your observations and check them by species?
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Well, I can’t quite compete with some of you folk who find the first known living specimen of a species. But as I was looking through my old photos, I found this one from 13 years ago: Genus Armacia, a member of Ricaniid Planthoppers. And it turns out that it is one of only five total observations of the genus on iNaturalist, of which two were by one user 9 years ago, and the other two just 1 month ago.
I attribute this find to my penchant for traveling to places that are not often mentioned in travel guides. The 9-year old observations are from Pohnpei, the 1-month old ones are from Palau, so mine fills in the geographical gap, as the sole observation of this genus in Chuuk.
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My rarest find is these alive Strongylognathus arnoldii https://www.inaturalist.org/observations/53846101, it is a poorly known slave-using species from quite rare genus and specimens that are known to official science (who knows what private collections can have) are those that were used for original description, and all info you can find about species is from their descriptor. So probably those are first photographs of alive specimens and probably one of the very few finds of this species.
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How do you tell what your rarest observation is? Is there a way to see what percentage of total observations yours are of a given organism?
No, not in an easy way, probably API can be used to show that, but you can search for endangered species right in filters on main page and you can monitor which species you met.
Well, in my above post, mine are exactly 20% 
I don’t have any rare observations myself, but one of my favorite observations is someone’s sighting of an incredibly rare snake.
An observation highlighted on the blog around the time I joined was https://www.inaturalist.org/observations/3911003 this Spider-Tailed Horned Viper. It was the first iNat observation of the species and is still one of only three.
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Define “rare”. There’s so many forms this may come in. In terms of birds, rare sightings is not all that… rare, just to name few I’ve seen in Oregon in the past couple years; Broad-billed Hummingbird, Wood Sandpiper, Broad-winged Hawk, Ruff, Whimbrel, Magnolia Warbler, etc.
If we take into account animals that can’t travel far distances like birds, the first one that comes to mind is Christ’s Indian Paintbrush. It’s rare because it’s entire range is about 20 acres, or in other terms, you can walk the perimeter of the range in 2 miles. My second best spot is probably a Rocky Mountain Tailed Frog. I’m not sure how many non-iNat sightings there are in Oregon, sources only say some places are suitable habitat, but it’s probably the holy grail for herps because of their elusiveness.
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I am the first to post pictures of Niphates olemda. It’s a pretty blue sponge. I photographed them in the Marshall Islands.
What surprises me is that it is very common in the coral environment in the Marshall Islands. However, I am the only one to have published it on iNat.
Only one of my three observations of this species obtained the research grade: https://www.inaturalist.org/observations/66341581
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I mean other factors such as willingness of the user and accessibility of location can also come into play, and that may contribute to the reason why even though it is abundant it is not abundant on iNat. Also cannot guarantee that everyone who visits the Marshall Island coral reefs are inatters too.
That is a very pleasing looking sponge though.
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One year my area had a drought so severe that the Sabine River at the local boat ramp was shallow enough to walk across. I noticed that the mussel beds were visible, and walked around that section of the river, photographing as many as I could. I am terrible at identifying mussels, but the people in the Texas Mussel Watch project are good at IDing things for me. One of the mussels I found was an endangered species, the Texas Heelsplitter. Another was the first county record of a Sandbank Pocketbook, another rare one.
I was later contacted by a scientist who was studying the Texas Heelsplitter.
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The rarest observation I have is of this tree Madhuca diplostemon from a temple about 15 km from my home. I went there after going to a nearby place for birding.
This is the only individual of this tree and was rediscovered after more than 180 years. This
mature individual was thought to be a common Madhuca neriifolia.
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As of today, I have a new one. I uploaded it some time ago, but only now did someone ID it to species. Assuming they are correct, it is iNat’s very first observation of Neolasioptera portulacae
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Cool!