@Yuillegan
Jim's thing is, how can I make Harry suffer.? So he's done the "punish Harry's women to punish Harry". A lot. It's old, move on. You can see a broad outline of whats coming next. Eb's irrational hatred of Whites. Harry and Lara's 12 dates. Do you see a trend?
Hmm. I see what you're getting at. I don't know that Jim will ever stop making Harry suffer, and therefore his romantic relationships are part of that. I think you're bang on about what's coming next. For instance, if Harry ends up falling for Lara I imagine Eb will kill Lara. If Harry doesn't fall for Lara it will turn into some burned hatred thing and their previously cordial relationship will be ruined, and Lara will become more of an out-and-out villain.
Should Jim keep making Harry suffer? It's a hard question to resolve. On the one hand, constantly torturing you're main character probably says a bit about how you feel within. On the other hand, there is nothing as boring as reading about/watching happy people. The Dresden Files isn't a comedy despite the occasional comic relief. It's a drama, a tragedy, perhaps even going for an epic (time will tell on that one). It's a hard thing to get right. How much pain is too much? By extension, we the readers are made to suffer which (so the theory goes) keeps us hooked. I can think of main characters I liked less for their victories, and hated for their failures and short comings. I can also think of main characters who were happier and less beaten up by life than Dresden, yet still remained interesting as they still had enough challenges to resolve. Does that make them better or more interesting? I think that's a bit subjective really.
Yes, I wouldn't mind seeing a few more wins in Dresden's life including romantically speaking. How about a long term relationship? Harry is in his 40s (I think that's right) and hasn't had a long-term relationship. He dated Susan very briefly before that went south, he dated Luccio for about a year before that went south, he dated Murphy for only a few weeks before she died (despite years of "will they won't they"). Elaine might be his longest relationship, and that was only while he lived with Justin. I suspect that was only a year or so as Harry left Justin around 16 I believe. Funnily enough, it's Deidre (who is currently in a long-term incestuous relationship with her own father) who points out that Dresden doesn't have any real long term relationships over his life. That's got to hurt a bit.