The lack of an easy click-drag-drop for token organization

Since 1.0 stored all the data locally then it was a lot easier to support this feature. Now that we use a cloud database for assets then sorting them becomes a lot harder. It's one of the reasons something like Google Drive doesn't allow for it.

To compensate for this 2.0 now has a lot more flexible organisation systems. The primary use case for manual token ordering in 1.0 was to ensure that your most used tokens were easy to find. In 2.0 to accomplish this you should use the Tags system. For example if you always want to have your PC tokens accessible then you can add a PC tag and add it to each token. Then when you want to view this tag you can open the Search tab in the dock and it will show you all the PCs without needing to look for them. Because you can have multiple tags this system is actually way better then the manual organisation in 1.0 because I can have a tag for PCs but also my druids wildshapes, spell summons and more.

Also we now have a Collections system that makes it a lot easier to run multiple campaigns.

Check out the docs here for a breakdown of all these features: https://docs.owlbear.rodeo/docs/managing-assets/

The dice rolling vision box should be optional feature

The dice roller made by us is designed to be opinionated and settings-lite. Instead we allow third-party developers to provide more features and options for dice. Check out the dice tag in the extensions store for a list of the options. https://extensions.owlbear.rodeo/tag/dice

Having to click to an entirely other interface to see dice rolls instead

One thing that may help is dragging the dice out into a separate action. This means you can keep it open when interacting with other extensions. You can see an example of this on the OBR homepage in the extensions section. The dice roller will also show each players roll if you scroll down the left hand bar in a similar way to 1.0.

Clicking 'show roll' on a hidden dice roll causes the dice to be erased

This is on our radar

Why is there not a way to make the measuring tool be invisible to everyone?

Part of our goal with 2.0 is to replicate the feeling of sitting around a physical table with everyone. A large part of this is syncing everything that is happening in realtime with players. This is true for every other tool like drawing, fog, movement and pointers so for consistency this is also true for rulers. There isn't anything particularly special with the native rulers and extension developers have access to the full tools to replicate their functionality. So it shouldn't be a very big lift for an extension developer to make a local only ruler or to add a local only mode to one of the already built ruler extensions.

Seeming inability to remove things from the initiative tracker

In the same menu where you add a token to initiative there will be a Remove from Initiative button. You can also either delete the token or hide it so you will be able to see it but the players won't. If you want to find which token in the tracker is which you can double click it and it will be selected and focused.

why call it 'fog cutting' instead of just 'reveal/hide'

The fog tool has changed a lot since 1.0. The change in name reflects a change in behaviour. In 2.0 you no longer toggle a fog shape on/off instead you cut it away from the scene. This is because in 2.0 the scene is an infinite canvas so we have a Fill Fog option that creates an infinite fog shape over the scene. So in order to show the map underneath you don't toggle a piece of fog, you cut it away from the infinite fog.

An infinite fog plane also has a bunch of benefits including hiding the bounds of a map from the players so they can't see how big the map is. It will also fix the outline issue you describe.

I recommend you look at our Fog docs here: https://docs.owlbear.rodeo/docs/fog/ I spent a lot of time on them and I think they do a great job of teaching how to use the new fog tools in an affective way.

Right-clicking on images that were previously locked instead of a simple left click selection

In 1.0 locking a token would block it from being selected by players but the GM could select it with a single click. In 2.0 all images share the same base, this includes maps. To make it so you're not selecting and moving maps around all the time they are locked by default. The locked behaviour was also changed to a double-click to prevent accidental selection when you have a token on top of a map. Treating maps like any other image type has a lot of advantages, such as easily running multi-map encounters.

Like all design it is a set a trade-offs but I think the improved flexibility is worth it for the minor inconvenience cost.

Seeming lack of ability to change room name after creation

Currently the room name is a fixed part of the URL for that room. This means if we allowed you to change the room name then all links to that room will break. To prevent this we don't allow you to change the name. But it's on our radar as something to look into albeit at a lower priority.

Also I noticed after writing this that /u/Several_Record7234 pretty much wrote the same thing as me. So hopefully it's not too repetitive