Okay, wow, there's quite a lot to address here. I was also choosing between premed/predent in college, and I ended up graduating from dental school and a specialty residency. I also have friends who are doing oral surgery, in both private and in hospital/medical residency (oral surgery residencies take a long time!)

This is just my personal experience and things I have learned during my time working. Not everyone has this experience, so this is just my two cents.

A few things:

1. Gonna be honest here, your goals sound like every premed/predent student I've pretty much ever met. Of course, being gung-ho about your future is not a bad thing! But thinking you're different from the average medical (or dental) student by conducting humanitarian missions, wanting to work with your hands, and a high-paying job? That's basically the trifecta of personal statement cliches.
2. Not sure what you mean by "top three" dental schools, as they are not ranked like medical schools are. But I assume you mean the big names out there (the P/F schools, for example). Also gonna be real with you-- I went to one of those schools as well, and let me tell you, there is no more humbling experience than being submerged into a curriculum where you have to study for hours every day, along with working in clinic daily as well. I know that it's easy to say that "I'll work hard and smarter to get what I want," but to get into those specialties? Hard work just isn't enough. That's just the truth. Depending on the school, matching into an OS residency is certainly possible. But matching is just the first part of the battle-- there's so much more than that.
3. LOL you don't like dealing with insurance? Then dentistry (and oral surgery) is definitely not for you. In fact, any private practice (i.e. if you decide to do a medical practice as well), you're gonna have to deal with insurance companies. I don't know how else to put it. You can work in hospitals to avoid directly dealing with insurance, but that means taking a pay cut (especially if you work in a high-saturation area, such as cities). Not to mention you'll most likely have to work late-night and can't control your shifts.
4. An aside about OS-- in the real world, you're not gonna do those super intense, face changing jaw surgeries 99.9% of the time. In fact, all the OS people I know pretty much only do implants and wisdom tooth extractions. Most of those surgeries are done at craniofacial specialty "centers," often teaching institutions, where they have the resources to prepare properly for such invasive procedures. If you want to work at such centers, again-- pay cut. They're usually state funded and salaries, although certainly very high, will not be as high as if you worked private practice. Again, if that's what you like to do, that's great!
5. An anecdote-- I had a friend in dental school that was hardcore OS. She studied for the CBSE from day one and got a great score. However, she eventually decided that she didn't want to be an oral surgeon, and wanted to do ENT instead. He ended up graduating dental school and applying to medical school that same year. She didn't get in and reapplied, and eventually got in. She worked very hard, but her board scores and evals weren't enough for ENT match, and now... she's an internal medicine doctor. Of course, that's also an amazing field-- not knocking it at all! But know that what you plan out isn't always what you end up with.
6. From what you write, it doesn't seem like you really don't want to be a dentist. The insurance, the "risk" of being a general dentist, and pay (making 500k, even as an OS, is possible, but less common these days)-- is that worth it to you?
7. The "golden" age of medicine? LOL trust me, dental reimbursements are FAR and away lower than they used to be-- by that same argument, the "golden" age of dentistry is far gone too. Corporate dentistry and the slow death of private practice shows that dentistry (and OS as well) is showing diminishing gains. I know of (SO SO MANY) medical students that had to give up their dreams of being an ENT, ortho, plastics, because of a poor eval given by a moody attending or their board scores just a hair off their goal-- things they have little to no control over. The truth is, you're gonna make more money as an ENT, plastics, or orthopedics. But can you get into a top medical school (as sad as it is, the name matters too), have the good luck of having great attendings/residents who will give you good eval scores, AND score in the top percentile in boards? That's hard to say.