I went years without any professional check-ups. When I finally made it to a dentist, they went "Cha-Ching!" and I maxed out a credit card getting everything done. At that point I needed 1 root canal, which is the reason I went in the first place, plus at least 8 cavities filled. A couple years later, I had 5 teeth removed, including the first root canal, and my wisdom teeth. All this was without insurance, and took forever to pay off.
I finally got dental insurance (not paid by my employer), and have since had another root canal and 2 crowns. The last year or so has been good, as I finally have everything currently dealt with.
Unfortunately, my 2nd son, @ 12 years old, just got braces last week, and I made the first payment of $995 for that. Even with insurance, braces are a bitch. I have another son who is looking at braces in about 2 years, as well. I hope to have the first set paid off by then.
Luckily, my wife has only needed a couple fillings in the last 20 years we've been together, so she's been cheap. My boys have all been good about no cavities, as well.
I sometimes wonder if having them all yanked and going with the fake smile is worth considering, as I can see that I may have issues with my remainder of not-so-pearly whites. My dad had that done @ about 60. I hope to make it at least that far.
Good luck with the teeth, and with life in general.