Do I need to tell the check in clerk that ...

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now more I think about it... I was given a room which is in need of renovation (quite worn), and when I leave my room the next morning the cleaner was right there at the corridor and watching me too !

Was it room 1408?
 
I did not dress up for business travel, just a small casual backpack....
a quick status run on the weekend, started 8pm Friday night ….

What's "dressing up for business travel" anyway? I will often, for example, leave home in evening to arrive night before, and most cases will be wearing casual clothing.

I think you're overthinking this. Is it big city hotels, or some small motel in the middle of nowhere?
 
I did not dress up for business travel, just a small casual backpack....
a quick status run on the weekend, started 8pm Friday night ….

Very few people in my industry dress up these days. It's been more than 3 years since I last wore a suit on a business trip.
Also I travel the world with something akin to a backpack with wheels. Again, you're not exactly special in that department, and I expect you'd have been forgotten by the time you got to the lifts.

If you really want to be remembered, just sprinkle in some low mumbling Latin chanting during your conversation with reception, alternatively leave a $1000 tip. Both are good ways to be remembered,
 
You forgot an option:

C. Meeting someone (later) at the hotel.
As an ex hotelier, one of the properties I had was on Parramatta Road, Sydney. It was not un-common for me to rent 15 - 20 rooms on a Saturday night between the hours of 10.00pm till 3.00am for single guys and gals. Quickest time the room was occupied was 26 minutes....it certainly wasn't used for suicide.....although if the wives found out, it would have been;):D
 
... so how can I remove their worry ? showing them my Qantas app and how close I will be a WP after this trip ???

Yes. And let us know how it went. :)
 
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