If you get title insurance in the future it would be in connection with an event affecting title, like a sale or mortgage loan. Drilling a well, by itself, would not trigger the need for title insurance.
There are times when title insurance can be skipped. Those times usually involved experienced investors, intra-family transfers, distress sales, very inexpensive purchases, or an attorney letter attesting to the state of the title. .
Title insurance is customarily paid for by the seller. It is the seller's way of proving they have good title to convey. The fact your seller is does not want to show you clear title via title insurance is a red flag that should be investigated before purchase.
Here's a tip: You should not be buying real estate from people who have a lawyer on their side without a lawyer on your side, too.
All the best,