I know it's sad that it's taken me this long, but what can I say? I'm a slow learner.
1) The academy is not a meritocracy. The ideology of meritocracy is just a screen that functions to keep the people on top on top...and yes, you can buy your way in. That's what I did. Namely, I bought my way into a MA degree program at a high-powered university with high-powered faculty that--open secret--has relatively open admissions. If your check cashes, you're in. Then I made certain that I became recognized as one of the department's top MA students. (Doing that sounds harder than it actually is, by the way.)
Remember, the academy is a small world, and all of the top people in the field know everybody else. When I applied to PhD programs in the same field as my MA, it wasn't just that I'd proven myself at graduate level work that made me a strong candidate. It was also that, as a protege of scholars who are friends of people on the admissions committee, I was already an "insider" of sorts; admitting me wouldn't be like taking a risk on a total outsider. I'm like a member of the extended family already. Even better, with a little bit of persistence and a lot of luck, you may be able to apply to a school as the former student of somebody on the admissions committee. (I did that too...successfully.)
In short, I have no delusions about my level of competence. I didn't get accepted to PhD programs "just" because I am smart and hardworking. There are a lot of people out there that are smarter and more hardworking than I am. I am where I am now because I knew people.
2) Go with the dissertation advisor that scares you the most. Nobody laughs harder at Jorge Cham's Piled Higher and Deeper than I do, but there's a serious lesson to be learned from the cowering cartoon PhD students who are endlessly terrorized by their dissertation advisors--if you view their terror as a state of mind.
Of course, being scared simply because your advisor is arbitrary, autocratic, and exploitative probably isn't a healthy relationship. But there are other--legitimate--reasons for being scared. Allow me to explain. In pursuit of advice and feedback, I have corresponded with many professors over the years both at institutions I've formally attended and elsewhere. Most of them I feel comfortable conversing candidly with. But there is one professor in particular that, excuse the vulgarity, scares the shit out of me. I stress out horribly whenever I know I have to email him; I'm scared to read his replies to me. A casual observer would think that I'm having a major cow for no good reason; his correspondence with me has never been anything but patient, kind, and supportive.
But what the casual observer can't see is how extensively this man's expertise overlaps with my research interests. It isn't just his excellent broad theoretical and methodological grounding. They all have that. He is expert in my area of study as well. So although we are not identical by any means, and it would be flattering to say that my work would complement his, not reproduce it, he could still use his extensive knowledge of the relevant subject matter to inflict devastating, demoralizing criticisms. He's never done it, but he could--and the mere prospect, no matter how remote, is downright terrifying.
The trick, I think, is to use that terror, and not let it defeat you. Channel it into a better paper--and use it when deciding who your advisor should be. Because the person most capable of ripping you down is almost certainly the person most capable of helping you scale the heights.
3) If you won't share the bad, then don't share the good. Some people like to brag about their accomplishments and conceal their failures. I've never been like that, and I have a visceral distaste for braggarts. If I don't feel close enough to you to confide my problems in you and to ask you for help when I need it, I don't feel comfortable telling you about the good either. (Of course, if I'm confiding in you, then it's a reciprocal relationship, and you can expect to be able to confide in me.)
Of course, being a freelancer is all about self-promotion, and I have learned how to blow my own horn when it's absolutely necessary...but lemme tell ya, I hate doing it, and it always feels self-conscious and fake. I'm nowhere near as good as those who can do it naturally.
But I've just recently realized that my distaste for bragging and braggarts extends to the behavior of others. Yes, I've gotten some great acceptances to top PhD programs. But all of these programs have major downsides, and making a choice is both complicated and stressful. Making good on some choices would also involve major sacrifice on my part. Therefore, do not boast your affiliation with Girl who Got into Big Name School if you're not comfortable telling those same people about the accompanying problems I'm now facing. And if you aren't willing to ask the people you boast to for help on my behalf--how f*ckin' dare you...! Unless you have a really compelling, practical reason (maybe you have a business to run, too, but you aren't trying to take the moral high ground), that sort of behavior is worse than bragging about your own accomplishments; you're just using me so that you can look good by association and boost your own ego. And at the end of the day, that sort of behavior deserves only contempt.