In my experience once a gentleman tells me they in a hotel I'm good, 2nd my Uber should be paid with card and share the rides details for tracking.

3rd: hotels don't really get involved on a normal situation I already know the room number or a gentleman would wait in a bar or reception. We do our things everybody is happy we done.

Thanks guys. Appreciate all your feedback.

Maybe I should also consider traveling to a working girls place instead of her meeting me. Any recommendations on safe reliable girls that work close to Monte. Preferably working from their own homes or a safe hotel. Not house with multiple ladies. Thanks.

Having worked in the Front Office Departement of Hotels and Lodges since 2000, I can assure you, one is way to busy to care about indescresions. Some guys even tell you what they're up to and ask to cover for them if wifey calls (which I did)
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It has become "industry standard" to pay travel costs upfront, for reasons already mentioned. Avoid being scammed by reading reviews and choose reputable ladies. There's the odd "vrot appeltjies" everywhere, although I think it's the absolute height of stupidity to scam a client our of a few rand, when you can rather go do the booking and make more money.

And with that said, happy punting, mate....Enjoy the finest Joburg has to offer