To to sumup, you would like the dimension tool to :
allow shortening of the lines
bring the text closer to the line by default
snap and stack. I figure you mean horizontally so they line up right ?
adjust the text distance from the line ?
Since you’re asking quite technical things about the dimension tool, I think it would help if you could show us screenshots of what you mean, a before / after or even just a big red circle on the issue (like they do on youtube)
edit yes, exactly this @PaulMcAlenan . images are simpler than words, especially when we don’t all speak the same thing