Fremantle
I've been attempting to do a few things lately that involve adding a whole bunch of photos to a wiki, with the aim being that there will be more information added about them at a later date.
The idea is to make it as easy as possible, so that the photography can continue. This sometimes depends on access to a decent internet connection, so it's not a synchronisation process (although I've experimented with that as well). The usual approach is to create a new wiki page, and use the MsUpload extension to dump 25 files at a time into a gallery, creating subpages that list 100 files each. The files are given names that we know are unique on the wiki, so there's no need to use the annoying interface to rename them (so that saves a fair bit of time). The slow parts are the uploading, as well as after saving the page when all the thumbnails are generated. But it mostly all works well enough.
The trouble comes after the files have been uploaded. MediaWiki's gallery syntax isn't the most flexible, it basically lets you have a thumbnail with a caption, and optionally a link that can go to somewhere other than the file's own page. Additionally, editing large galleries like these via VisualEditor is really not fun. So how best to quickly add notes about each photo (or sometimes, groups of photos), when those notes actually properly belong on per-photo description pages? We don't have time at the point of uploading to create those other pages (the idea is that all the extra metadata can be derived from the photos, and it's only the 'special' metadata that we want to capture right away). It looks like it's going to be some sort of custom 'gallery-like' template, a bit like how the G template on Commons does it, with weird custom parsing of pipes and newlines.
Then each photo can be rendered with an accession number that links (along with linking the thumbnail) to either the record page after it exists — but more usefully, before that exists, to a preloaded edit link at which the caption and other info can be added.
(I'd planned to put the actual template here… but there's other stuff going on today, so it'll have to wait….)