We're in a different state but we did just recently have a well drilled. Beforehand we asked a lot of different people for their recommendation, then I called the different drillers. I asked a lot of questions especially about the price, how far did they think we'd need to drill, what if they didn't find water etc. The big company said it would be anywhere from $12k to $20k! Talk about sticker shock! The others were a little lower but not much. Someone told us to wait till winter when they didn't have much work, maybe the price would drop. So that's what we did, and I kept calling around till I found a small outfit that gave us a bid of $6k to $12k. It was near the end of winter by then. And this guy took time to explain it all to me, PLUS he answered my phone calls, in general much more helpful. They came out, drilled and hit water at $6k. Such a relief! I was worried that we'd end up with a dry hole. We get a gallon and a half a minute which is considered a decent well here. I thought it was kinda low, but he said we could get a cistern and just run the pump till it was full. A gallon and a half per minute will add up pretty fast.
A driller can get records of all the wells around you, how deep they had to go, what type of soil they encountered etc so they can make an educated guess on your well
Oh, and one other thing, before I bought the land I made sure to ask the R.E. agent, seller, and land office people if it was ok if we drilled our own well. " Yup, yup just fine." Well after we bought the land we found that we could drill the well but not use it unless it was Permitted. Which the Gov won't do unless it was signed off on by a licensed driller. A drillers not going to take the responsibility on a well he didn't drill. So that may be something to check out.
I hope it goes well for you. Functional plumbing is a wonderous thing!