I mean... To be perfectly fair, DSP did manage to catch Leanna, but she was REALLY young when they started talking. Impressing an 18 year old when you're flush and at least somewhat confident is not really that big of a deal. The way Panda talked on online forums, she really liked Phil... But the money didn't not help, if you catch my drift. She admitted to wanting a comfortable lifestyle, some spending money, and being really horny. By the end, she was even openly complaining she was not getting enough.
If you're 18 and you're offered a free ride, sex, a cool house, and help to set up your own business... Fuck, I figure that'd be really hard to turn down. I have no doubt that had Panda struck out as a let's player, or became a rich soap tycoon, she would have definitely stayed with Phil, as long as the deal didn't change. However, Panda grew up, and settling for Phil started to look more and more like a terrible idea. The deal had changed, too. And the realization that the most the person you've loved for years would do for you if you had a panic attack would be try to monetize it, come to the hospital and eat your sandwich must feel like a kick straight to the nuts.
DSP's on the low side of average looking. I'm sure we've all seen prettier and uglier guys. It's his personality that turns people off, and I figure he's at least decent at putting on some superficial charm for a wine n' dine deal. He's also a compulsive liar. I seriously doubt any Kiwi reader would date Phil knowing all the shit he's pulled, unless she was also a shitty person herself. You can google Phil Burnell and the first page brings up the lolcow wiki. You can google pigroach and it's mostly images of him! That level of public scorn is kinda hard to shake off. Whoever willingly goes through with dating Dave either knows or doesn't even google. To make matters worse, Panda was good looking and fairly charming when she wasn't trying to be a Dave knockoff. The only thing that would turn people off was the skull-piercing voice. Phil knew this, and probably felt threatened. Then the last-ditch marriage attempt happened.
From what we know about Kat, she's probably had it a little rough. She depended on Subaru Man, and that relationship was floundering. She even came about as clean as she was gonna on stream. "I love being here with DOT DOT DOT -Idea lightbulb- Phil. It's a real improvement over where I was before..."
Really, I think Kat latching on to Phil as a provider for the short term makes perfect sense. Phil's being weird about it. Kat's dropped the "I want to stream too" bomb on his lap and he's dilligently ignored it instead of working out a schedule for the both of them to have turns on the business line, business PS4 and business PC. I feel to Kat, if she can make it work with Phil, become a streamer, and make the big bucks, great. She might even stay with him out of gratitude, though I wouldn't count on it. To Punished "The Guy" Philip however, Kat's nothing more than a trophy, a dangerous trophy that brings all the Tyrones to the yard, so she needs to have limited access to the internet, protect her powerlevel, share nothing, blog nothing, and DEFINITELY do not stream. Kat's positively odd looking, boring and smacks of being a "fake gamer grill" who just nods and likes everything. If Phil wasn't so spooked by Panda leaving, he might have been more normal about the relationship.
But really, not letting your SO do what they want, specially when it is within your means, SPECIALLY when it wouldn't even be any extra spending, just LITERALLY LETTING HER TAKE TWO HOURS A DAY ON THE BUSINESS STUFF, is a guaranteed recipe for failure. When Kat skedaddles to the next sugardaddy, she won't even have a linger of a doubt that this is the right move for her. After all, Phil was just a stepping stone, and he didn't even let her give streaming a go. What an asshole.
TL;DR: Dave attracts vulnerable women pretty good, but I doubt he could land a normal one. Even if he did, one google search and it's all over. Panda was too young to know better, Kat doesn't give a fuck because she needs support. I'm sure if we ran a tinder-style poll between Aris from ATP and Darksfadil, the former would get more hits.