Hi bro,
I'm not experienced in Geylang, so I can't answer your questions well. Specifically, I wouldn't know whether you'd be a target for local law enforcement.
But seeing that you're here for a holiday, I'd say go for the best - Orchard Tower. I've walked around geylang a few times, and honestly, the standard of local ladyboys just doesn't match up to that of the thais working in OT. The price of course, can go up to 3-4x as much. If you're an experienced punter, which you sound like you are, you can probably get a good deal or two there.
Where do you hail from? Have you considered buying a cheap ticket and making a trip to bangkok? Much more goodies there to be savoured, and at much lower prices
