You do follow the Hi with a question, right? You're messaging the person because you have an actual question, I'm assuming.
Why not just combine them into one whole message instead of dividing them?
I'm not sure I understand where the lack of practice thing comes in.
But if they’re going to ask the question anyway, what’s so hard about just typing “Hi,…” then ask whatever rambling or imprecise thing they’re going to say before hitting enter? No one is requiring it to be concise; it’s just that they got our attention with the “Hi” and now we’re waiting five minutes for the question to be asked, instead of the question, in whatever form, appearing without the preliminaries.