Write with the page you are looking at, the month you are travelling, and what you need to know. Short messages get short, useful answers.
What to put in the first message
The month or dates you have, where you are going, and how many of you are going there. Add what cannot flex: a fixed week off, a booked event, someone joining you from another city. Ages are worth mentioning if the trip involves long walking days or trains that leave before eight. If the question is about a checklist rather than a route, name the list and what you would add to it.
Corrections first
Roads close, trains get re-timed, a trailhead parking lot fills by eight. If you found something out of date, send what you saw and when you saw it, and the page gets fixed.
Route questions
For questions about whether a plan works, include how many days you have and whether you are driving or using public transport. That is usually enough to say whether the trip is realistic or needs one more day.
What happens after that
Messages are read on working days and an answer usually lands within two of them, sooner when a page is plainly wrong. If a route needs more than a paragraph to judge, you get a question back instead of a guess. Nothing is booked or paid for through this site, so the reply is the plan as far as we can see it, and it comes from whoever wrote the page you asked about.