Currently we can use read convention to have a vertical dimension's text set to Horizontal. What cannot currently be done is have a horizontal Linear Dimension text align Vertically.
Something close can be done with Setting the Dimension String Type to Ordinate and then use Ordinate Dimension settings and set it Parallel to Witness Line. The problem I am encountering is if I want a series of dimensions Say 2' - 0" to be read vertically. In ordinate it reads 0, 2', 4' 6' etc... Instead of 2', 2', 2'
While trying to fix this I was considering making the text blank and using the text tool and rotate the text that way. But There were 100 Dimensions it was not Realistic. This brought me to another feature request. Turn off Text option. Right now people are doing the following: click the dimension, then set it to "Replace with text" and then right click the text area and "Insert unicode character", "unit seperator".
The problem with this is you have to do it for each Dimension... again with over 100 dimensions.... Not useful.