@Ned Carey @Tai Bhattad
I filed the Quiet Title myself, but only after I've quieted a couple others using an attorney before, and took classes from @Denise Evans. The judge even asked me a question about the paperwork that I would not have been prepared to answer had I not asked my attorney the same question on a previous motion.
To be clear, I have missed things in my title searches before. Just because you hire an ad litem doesn't mean they are going to spend a lot of time on it. The title search company is going to do a full search regardless of a quiet title, and will not insure if they see something the quiet title didn't specifically address.
The title insurance company did not care that I filed it myself. They had two issues. The smaller issue was that it was a default judgement. They would rather see a defendant take action and lose, because they are afraid someone could argue they weren't probably notified in a default judgment. To Denise's point, the quiet title should stand, but the title insurance company would still incur costs to defend. The major issue was that the tax deed was not 3 years old. Again, they may be able to argue the quiet title stands, but they would still have costs to defend.
As an update, I may have found an title insurance company willing to cover. I'll update everyone if it goes through.