Avernite - just because Harry fights for good doesn't mean that he doesn't aid his enemies goals too, not everyone good is allied and nor is every evil villain or group. The point is that it is complicated. Lara constantly aids Harry as he removes her enemies often for her, she wouldn't be running the White Court without him. What he did was a well intentioned act, perhaps even a morally (in the divine sense) good act, when he fought Lord Raith. But the outcome is that Lara rules the White Court. And as we know about magic (from like 10 WOJs) good is more about result and intention, at least in the Dresden Files. He has also willingly aided Mab, Nicodemus, Marcone, even the Red King (for about 15 minutes when he was killing Ariana for him). Harry doesn't like to think he is a politician, but he makes compromises to suit him and what he believes is the Greater Good all the time. Whilst he might be doing good overall, doesn't mean he isn't aiding the various bad guys sometimes. It is no coincidence that his ID is morally ambiguous at best.
Uriel's involvement is more significant that a pep talk or a pat on the back. He fights for souls. Consider he pretty rarely shows up to anyone at all, and is supposed to be the most quiet archangel. Yet he is showing up and communicating more and more with Dresden. I would say that isn't coincidence either. I think he is doing his level best to fight for Dresden to be on the side of the angels, pardon the pun. I think Dresden's significance in the grand scheme of things is not to be underrated, which is why so many higher level beings show interest in him. As Vadderung said, he is a fulcrum. I think Uriel's constant encouragement etc is one way he can constantly keep Dresden from falling into darkness. Consider without Uriel's pep talks that Dresden might have continued to doubt himself, gone down worse paths, made worse decisions. Harry constantly is aware of how a few words from the greater, older beings can have enormous impact on him (especially if they are "evil") but it isn't like being "good" would mean you are a slouch. Uriel is just as impactful with his words, if not more so. He told Dresden that Maggie was actually his daughter. Consider the repercussions of that, and what might have changed had he not.
Bad Alias - I get your meaning and I agree. Sometimes he means to, sometimes not, sometimes it doesn't matter as the result will stay the same. And you are absolutely right, I think you manipulate Harry at your peril. He is too unpredictable and too erratic for most villains, even the logical ones. Sometimes though I think his most dangerous foes are the ones who understand him too well, understand his drive and his sense of righteousness and his failings and his strengths. People like Marcone and Kincaid, and Lash. Probably others too that I am forgetting. Elaine makes the list because of her behaviour in Summer Knight. Molly would too, had she stayed a wizard. The know his strengths and weaknesses, and are learn from their own. Harry fails the most when he can't see past his own blindspots.