Edit 17 days later into Escort Saga:
A (((drunk))) stream and sober trashtalking stream later he's now thoroughly drug Leanna through the mud so it's definitely not her, but if it isn't an escort and it is real (which I'd be willing to believe) then it's going to be hilarious when she realizes his full internet presence and all the shit he's been saying about her. His plans for her servitude will be a huge shocker.
EDIT Post Escort Saga: Yeah, I did it. I'm calling the escort saga dead. She got her needed leverage to make him sweat via like 40 spergy dudes who loosely keep up and troll tip/etc.
From here on out it's just attention probably and if it is the only ones to blame are the thirsty dudes who give it.
I think it's probable that this Tiffany is a goose chase, so perhaps we're back at square one for figuring out who the mystery girlfriend was in the case that the escort was a ruse cruise for all involved.
@neger psykolog had it right with his deck/dealer metaphor, only I'd like to amend that we're either the deck and she's the dealer, or we're another sucker at the table like DSP and she's still the dealer. Was a fun ride either way, and I really hope it was her.
I'll be awful sad if it was some impressionable little girl.