What you describe in your opening post has been a conspiracy of major pains in dcad since forever.
What happens is dimensions automatically orient to the front (and right, I think) so rear (and left?) views show the dimensions backward.
I have managed to avoid dimensioning in 2 axis for years, so to avoid this problem, but just yesterday I couldn't avoid it and had to come up with a fix.
What I did was draw the dimension in 3D then place a 3D Text entity so it orients like the dimension's text, but face correctly. Then I went to the info box's second dimension page, activated the 'Fixed Text' field, copied the text, then backspaced it so nothing shows. I then pasted the dimension text into the 3D Text and grouped the two.
The obvious drawback is if you adjust the dimension you would then have to deactivate fixed text so you can copy and paste into the 3D text, then make it blank again. Also would have adjust the location of the 3D text (but generally the dimension text don't automatically adjust anyway). But it's worth the trouble to have the text oriented properly.