Well... I finally went to the dentist for the first time in my life today. I never had insurance as a kid (or young adult) until my wife got this new job about 3 years ago. Since then, I've just been putting it off, but my wife made me promise to go after the new year.
I'm happy to report that, much to my surprise, my gums are in good shape and so are my teeth. I have one tooth that might need a root canal (it isn't hurting at all... none of my teeth do) and a couple that need minor fillings, but nothing major at all. The dentist also recommended the Sonicare and so I got one from his office for $80. I went to the local Rite-Aid afterward to get some more toothpaste and saw the same model for $129.99, so I got a good deal.
I'm going in for the cleaning and root canal in a couple weeks. I was pretty nervous about the whole thing (and lied through my teeth about being so to the dentist and assistant) but I'm very happy that everything is mostly ok. That's pretty amazing for almost being 29 years old (and eating as many sweets as I do).