Hi Brian,
Thank you for the model and concise list of examples to try.
I have good news, it appears that all the the annotation issues you are reporting there have been corrected in the daily build that we test internally. That means that it should be in the WIP that you download by next week.
This was reported last Friday by Alex here. (We owe him a beer or a box of chocolates.) After much of back and forth, a few sleepless nights, I saw an internal build here on Wednesday morning that I believe solved these issues.
If these annotation features are important to you, do not save your models from the current WIP. The changes that fix the issue that you report, happen during import or open. So if you have saved and your model’s annotations are messed up, go back to an earlier version of the file.
This is what you will hopefully see next week. So you will not see this in today’s public WIP. But it is definitely something to look forward to and test next week, once the WIP is released. (But I am out of the office next week, and I want you to have these details before I go.)
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New Model Space Scale
We now have control over scaling in Model and Layout space.
I think it look like Rhino 5. I only had to to a little dimension grip edit to get it to look exactly.
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In the next WIP, on Options-> Doc Prop -> Annotation, you will see Enable Model Scale.This actual give one level more control that we saw in Rhino 5. You can completely turn any annotation scaling off. Also when imported, text actually gets a Model Scale of 1, as an “override” of the Annotation style.
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Just like in Rhino 5, turning on Layout space scale could be a disaster, if the model was setup to not use this type of scaling. Text was scaled to the 1:1 height, that could be 50mm or 12". If you decide this is better, then you have some work to do to update the model, and you simply may not want to.
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The only other issue I saw was the dimensions popping to the right, and all the arrows over lapping. I will post it for the developers. I was able to grip edit the locations of the 50’s, and override the arrow on the dim of 150. It seems to be looking quite good now.
I may have something wrong here since it is all new - so others can pile on and set me straight. 
And I still need to look at the text wrapping issue… but I want to get this back to you ASAP.
Thanks again, Brian.
Sincerely,
Mary Ann Fugier