Hey Taj,
It's a great suggestion to improve what Roll20 has...
But also, from the Wording of your suggestion, to a large extent, Roll20 already has that. Maybe you aren't aware of the features Roll20 has (Group and Ungroup, not to mention API Mods available for a Pro user like yourself). Or maybe you know those features and your Suggestion is for it to work better, which I would agree. If the Suggestion is for improvements to the current system I think your post could be made more clear about the exact nature of the changes you'd want to see and refine the title to hammer directly on that.
From your examples it's either a Wizard with a Status icon overlapping, or a Party of 4 PC Tokens side by side, or a PC Token riding a horse/mount:
How to do the Group and Ungroup that we already have:
- Multiselect first -- Drag to select 2 tokens (or multiple tokens), or hold down your Shift key while tap-selecting several tokens,
- Right-click > Advanced > GROUP.
- Now they are grouped. This was the heart of your Suggestion, the way I'm reading it.
Move the group around to test it. This is where you may find some limitations and issues that could be improved with better features, and which could form the title of a new Suggestion. The biggest problem is you can't really control or access Token Bubble or Token Marker features of the individual tokens without Ungrouping them. So you can't easily change the HP of 1 party-member in the group of 4, directly on the token itself (of course there are other ways and places to change the HP so you aren't blocked from doing it, just can't do it on those little 3 token bubbles while it is in a Group). All you can do with the group is move the whole group at the same time, so the 4 move together nicely, and even rotates nicely. And, you can even double-click on a Token that's within it to get its Token Settings (which again, contains the HP and is another way to access the HP or token bubble number values). But a drawback is you have to UNGROUP every time you want to Bubble-or-Marker-or-Reposition an individual within the Group. The same problem is on the wizard with the status icon grouped, you can't change the Wizard HP on his token because he is Grouped with the status icon. If it's something you plan to Group regularly (using status icons Grouped with a token) then I would advise to have routine workflow that doesn't use Token Bubbles (so adjust HP elsewhere).
By the way another whole route for you (with Roll20 PRO) is the API Mods. There is a Mod called "Mount" that works better than Roll20's Grouping feature, for the mounted situation. There are several other Mods like that with differences designed for carrying a torch, following another token in a preset marching order, and other such fancy tricks. Look in the "one click" for the Mods or start reading-asking in the API Mods sub-forum for more info on those.
