I really miss this feature and would be great to see it in Sublime Text.
your first issue can be adressed by writing custom command, which i did a few months ago.
take a look here - https://gist.github.com/3478311
Vitaliy - Thank you! Very useful while waiting for this to be implemented (fingers-crossed) in Sublime Text as a core ability!
You can find updated version of the command here https://gist.github.com/4338959.
It supports mltiple selections as well as fixes one exotic annoyance i had with new regions placement when expanding selection.
Another big +1 :) Bit of a showstopper for me - I've been used for so long to freely being able to place the cursor and type, originally back in the 80s with Brief and now with Crisp, the multiplatform Brief-like editor that I've been using since that time. Apart from freeform column selection and insertion, this function is also very useful for in-line commenting and general processing tasks on SQL, CSV etc. types.
I've been "playing" for a little while with Sublime as I liked the innovations that Textmate (and E on Windows) brought to the table. My needs are for multiplatform and the least important to me is Mac, so TM is ruled out. E is Win only, and has a tendency to be slow and buggy while its development cycle seems to move like molasses. Sublime looks just about right, but is missing a few key abilities; for me, as for a few others this is a big one.
As a workaround I did think to knock up a script (enable freeform mode) that would populate the RHS with spaces up to column x, and disable freeform mode that would strip them again. This would be a useful stopgap but problematic for working larger files.
On another note, and disappointed by E in this regard, I was wondering whether development on Sublime had slowed up. I noticed Jon hadn't posted here for around 8 months. I'd be much happier buying into something that really feels like it's an active, ongoing development.
By the way, this can be implemented as a plugin. Completely (assuming you have "trim_trailing_white_space_on_save" active and I did not miss something).
The keys are with the viewport and layout methods from View, some math and the overriding of the "invisible" "run_" method so you can parse the "event" parameter which is silently stripped before calling the "run" method by "sublime_plugin.py".