Jess
I appreciate your suggestion, but I disagree that displaying a photo for all the entries in a day is a better solution than simply being able to select a cover photo manually. I can see multiple problems with this proposal.
At the moment the calendar widget on PC shows about a month worth of images. One image per day. That is about 30 images on screen. If there were 4 images per day instead then there would be 120 images on screen. This would make it a lot harder to distinguish the boundaries of each day, and it would overload the interface with excessive information. I have a decently big monitor and I am not sure if I would like 4 thumbnails with 1/4 the size of the current ones. I feel like they would be simply too small and too many.
On a mobile phone this change will straight up make the calendar widget unreadable. Mobile interface already has a really small screen to work with, so the picture size in the calendar widget is tiny. If instead of one picture you were to fit 4 smaller ones, then the pictures will become simply miniscule. Additionally, the mobile app fits 2 months on screen. With 4 pictures per day, that is about 240 images on a small mobile screen. This will not be readable at all.
Another problem with multiple covers per day is the blank spaces. Like I have written above, the primary reason why I prefer Diarium over Obsidian is the beautiful overview of my month with most important pictures for each day. If a user were to write 2-3 entries per day. With the current method of only one image per day the user will have a pretty and completely filled out calendar widget. If there were 2-3 entries displayed per day instead, then the calendar widget would look like a half filled checkerboard. About a half or a third of the calendar widget would be filled with just a blank space, even though all the days have entries with photos.
A thumbnail bar for 5+ events will not fit on mobile. There is simply no space for it. While it can fit on a PC, but it will introduce some problems. At the moment when you click the day in the calendar widget it simply opens up the list of all entries in the day. If an interactive element is added to the day in the calendar then it will require additional precision of interaction. User may accidentally click the scrollbar when he tries to open the entry list or vice-versa. Users may accidentally misclick the scrollbar and open the entry list instead.
Another problem with a thumbnail scroll bar is the redundancy of this functionality. The ultimate functionality of a thumbnail scroll bar is to show only one cover while providing the ability to see all of them if needed. But... we already have this functionality. The calendar widget shows one image and if we click on the day then the entry list for this day will be shown. In the entry list for the day we can see all the thumbnails for the day as well as their titles. No awkward scrollbars and we already have this functionality.
This also introduces extreme calendar interface inconsistency. At the moment the calendar widget has a clean look with only one image per day. If multiple cover art support is introduced then it will become a mess. Some days will have one image, some two, some four, and some will have a scroll bar on top.
There is also a technical problem with this proposal. My request is pretty simple in comparison. I just want to be able to select which photo should be on the cover of the day. That change does not require any interface modifications or any other drastic codebase changes. But even so, even if the feature is simple, I have already been waiting for it for almost half a year. And it is not even being considered as far as i can tell.
Multiple thumbnails support will require massive rewrite of the code and a lot of interface changes. The entire calendar widget will have to be reworked and rewritten.
Even if we ignore all the problems with the multiple thumbnails, this is just too much work.
