Not much to wonder about there - the guy is severely disabled and had escorts turning him down because they were uncomfortable with a disabled client. I remember when I first started doing this, one time I got stood up and the first thing that rang through my head was, "WTF, I can't even pay to get laid?!" But that was just a fleeting thought I had out of disappointment. So imagine never having had a girlfriend before (not 100% sure, but likely here), and you offer money to girls where they tell you straight up, no thanks. Gotta fuck with your head. This girl comes along and is ok with it, and then leads him on to believe she really likes him.
Ain't hard to see how he would fall for this - sensible, intelligent people still get conned regularly - but at a certain point you gotta wise up and realize something funky is going on. Remortgaging your home to send tens of thousands of dollars to the Dominican or wherever not once, but multiple times? C'mon...
I think we all get suckered doing this in one way or another. Like when a girl is urging you to fuck her faster and moaning obscenities, it's not always because she's close to climax, she's really encouraging you to hurry the fuck up and blow your load. Works like a charm though and we ignore it because it's ok for the moment (unless it's really obvious). Some guys are pretty lonely though and if a girl is a predator like that, she'll sniff them out and start sucking them dry until the guy catches on. This dude never did until everything was gone and even after that she took it a step further and destroyed him emotionally. Killed in a car accident at xmas thinking she was carrying his baby? Wow. The one thing I do admire about this guy is that he didn't roll himself into moving traffic, and then put himself out there for embarrassment in order to pursue a conviction. That takes balls.
Poor guy will probably never trust a woman in his life again though.