What has always annoyed me about this is that < and > (de)indent but also unselect the text and put you back in normal mode. Why? I often want to indent more than once but don't want to count ahead of time how many it will take, but that means I have to reselect the text N times. Is there a good way around this?

Edit: just found that gv will reselect the last visual mode selection, which makes this much less cumbersome.

Why don't you just hit . to repeat the last indent?

This is the super easy way to do it.

I like to us gv as default, so I have this in my .vimrc:

" Align blocks of text and keep them selected

vmap < <gv

vmap > >gv

I think my comment wasn't super clear. What I meant is shift-tab in terminal emulation, which wasn't registering correctly.