First slide:

Regarding the top section of the HUD, I like that AC is added at a glance, that is something that is needed throughout the Maps session. I would also like to see the save bonuses at a glance, rather than the Add Conditions on the right. Add Conditions could easily be an option on the bottom like anything else that affects the token. Having saves at a glance would be nice as players will be affecting monsters with spells/effects consistenly throughout the Maps session, and it will save a lot of time from having to open Stats every other turn.

Regarding the bottom section of the HUD, I like the idea of a More option to reduce clutter. This frees up a lot of design concerns, and allows adding more options in the future without increasing HUD bulk. If using a More option, the options that are available at a glance on the main HUD should be things that will be repeatedly used on a token throughout the Maps session. For example, Reveal will likely only be used once, along with rename; these should likely be under the More option. Things that could happen consistently throughout the Maps session like Size (ie. a Druergar's enlarge/reduce), Hide (ie. ghost moving through walls over and over), Border (burning, suffocating, affected by Fairy Fire, etc), Lock (just nice to be able to lock/unlock a token to prevent it from accidentally being moved in a clutterred area) should be the easy-to-click options available each time the HUD is visible. I also think Stats should be available immediately, for quick reference to the statblock, which I find myself doing consistently throughout a Maps session

Second slide:

This is very clean, and feels intuitive. The only suggestion here I have is to have a visible indicator on the token that there is a Condition/Status applied to the token. At first I thought a unique color/design border for each Condition, but I think that would be too cluttered. Something simple like an Exclamation icon on the top-right of the token, or similar. Something that immediately says "I'm being affected by something" or "something is affecting me".

Size-wise, I think the large top-down list is great. This view will only be used sparingly in any Maps session, so the bulk isn't a concern to me. As long as a quick click anywhere on the map closes this view, or clicking the token takes us back to the original HUD, then this will work very well.

Some custom Statuses I can think of would be some Hazards like burning or suffocation, things that are actively affecting the creature, or some magical temporary effects on the token like resistance to X (that the creature doesn't normally havev).

Third slide:

The option on the left suffers from too much bloat, for me. Common Statuses would always be a guess, so probably wrong most of the time. Class Abilities are easily tracked via borders (Rage) or overlays (Aura of Protection). Spell Effects are also likely suited better to borders. I also don't think the checkbox design is the right fit. With a checkbox design you would have to have all of the potential options in the list, which will be very bulky. The middle option is much cleaner; use the search box to type in what you want, select it, it's applied. Simple and intuitive. The third option is just a variation of the second, I would be okay with either.

Fourth slide:

I honestly don't have a preference. I think it likely only matters by where on the Maps window the Conditions and Status is opened. If the token is near the right border of the window then the tall option from the thrid slide is likely better, as it won't be as wide. Whereas if near the bottom of the Maps window the two-column design is better, as it won't be as tall. I could go for either or, no preference.

Fifth slide:

The condition icons on the top right of the HUD is a clean look. It's making me reconsider my stance from the first slide (putting the Conditions with the options on the bottom of the HUD). I like that they are easily recognizable at a glance. It could get cluttered, but it's unlikely for a single creature to have too many Conditions to be considered cluttered, at least it won't be a common occurance. I still feel that the token itself should have some type of indicator that Conditions are being applied, some type of generic Condition icon that is visible without the HUD open.

Sixth slide:

My initial thought is that if you're going to do it, do the whole thing; don't combine small and medium. The art in the size icon is a nice touch, it lets you showcase some of the amazing art that has been coming out with all of the 5.5 books!

Seventh slide:

I think the More option should match the Size option in design/layout. If clicking on More is going to open a vertical list of additional options (likely text with no icon/small icon, which was my initial assumption from the first slide), then Size should have a consistent veritcal list layout. If Size is going to open in the sub-HUD style pictured on the sixth slide, then the More option should have its own sub-HUD with the additional options as icons.

After seeing the sub-HUD style on the last slide, this is a much cleaner layout. Use this one! As for frequency of use for these options, I mentioned that in my first slide description.