Any idea around how long 1 would take? If we did 2 would that also speed up my system? Just trying to think of pros and cons
Speed up your system? No, that would be highly unlikely.
How long it would take? The filesystem check when you first boot I would anticipate taking at least 10min. The actual resizing... That's hard telling. It may not take as long as I'm thinking since the whole latter part of the drive is basically empty and all it has to do is be extended.