Upon review of RAW, I believe every table at which I have played has misinterpreted how druid wildshape hit points work. The "ah ha" is in bold below.
While you gain the hp pool of the beast form chosen, RAW does not specify that the beast starts at max hp; merely that it has a different pool. It also doesn't specify that each beast form uses a different hit point pool; merely that it is distinct from your humanoid pool.
So if you use a dire wolf form with 45hp, you don't get double that per short rest. You get 45. If that form is wounded for 33, those 33 will need to be healed.
Further, a Moon Druid (using Combat Wild Shape) can expend spell slots as bonus action to heal the beast form. We mostly ignore that because it is unimportant if your beast mode (wrongly) starts at full hp every time. However, if beast form did indeed start at full, then to heal using the fewest resources you'd just use 2 bonus actions to flip to humanoid mode, back to beast mode to start over at full. Given the way players may choose the timing of spending bonus actions, you're only "stuck" as humanoid from end-of-this-round to the beginning-of-next.
Essentially we've been treating the beast mode as temp hit points. Instead, I believe this is the way it is intended to work:
1. Your beast form has a separate hit point pool. It is not specified, but my personal take on this is you have one pool for all beast modes.
2. Damage to that hit point pool does not heal on its own. (If you try to take a long rest as a beast, a druid cannot remain in beast mode for a long rest due to automatic reversion to humanoid when you become unconscious.
3. If you try to assume a beast form with fewer hit points than damage from your pool, you go unconscious and revert to human form. (Interestingly this can leave you unable to assume beast form until someone else heals your beast form before it reverts to humanoid. That time is the time to perform 1 action or possibly a bonus action for a moon druid, which means a healer can ready an action to perform the heal, provide a healing potion, apply a healer's kit, etc.) I would permit a moon druid to expend spell slots to self-heal upon changing form, though I am not sure how a land druid could do so. I suppose I'll consider that when someone plays a land druid at my table.
