@cygnusa, it looks like you use Adobe Lightroom, so I would recommend geotagging your photos before uploading. There’s a tutorial and discussion here: https://forum.inaturalist.org/t/geotagging-photos/66
As far as I know there is no limit to the number of pinned locations. If there is a certain location you can’t find, please let us know here or at help@inaturalist.org so we can investigate.