Steve The Plant Is Doing Pretty Great, But Does He Need A Trim?

Haaaalp, gardeners of Sedalia!  I need to pick your brain!I've introduced you to Steve before.  Steve lives in my office on top of a filing cabinet I don't use.  He's been through a lot.  We've been together several years now.  There was a time when I thought I might lose him (I moved him outside, he didn't like that at all).  But now, as you can see, he's doing well!

In fact, I worry he might need a haircut.  The main problem is, I don't know what kind of plant Steve is (in our relationship, I have respected his privacy).  So it's kinda hard to Google "green houseplant care" and get results.  So that's where I turn to you guys, the green thumbers.  I have questions.  Should I trim Steve, or let him keep growing?  Will it be bad for him if he touches the floor?  If I do trim Steve, can I do that thing where I put him in water and then Steve's twin will grow roots?

He's doing pretty well up top, if that jar thing works, can I replant him.. with himself?  Should I get a bigger pot for him?  Jeez, that IS a lot of questions.  I just want to be a responsible plant owner, Steve deserves that.  Green Thumbed People, please, help me!

Plantingly yours,

Behka