Don't ever have a well. City water services are much easier; if you pay the bill every month, you'll have water. You won't have dry taps and a well driller in the hospital.
Every summer, our well starts to run dry in August; we have enough to run the house, but not enough to keep the lawn from turning brown. Three years ago, we almost re-drilled the well, but figured out that if we got a fancy new sprinkler controller, we could avoid the hassle and expense. This year, we started running out of water in June, and by August, we were too low on water to run the house smoothly. It turns out that our water level has dropped from 165' below the ground surface to 215' down - in a 220' well. So it was time to redrill the well; we would drill back down the same hole rather than drilling a replacement well because redrilling is cheaper and the paper work for the DNRC is easier.
Our favorite well driller put us on his schedule, fitting us in soon because it was getting urgent. He said it would be a two-day job, possibly three if things didn't go smoothly. On Monday evening, they brought the trucks up. Tuesday, they pulled out the fence and a couple small aspens, set up the drill rig, and pulled the casing out of the well. Wednesday, they drilled to 310', but had trouble putting a new casing in because the sides kept caving in. Thursday they tried Plan B to get past the cave-ins, then went to Plan C (this is starting to get expensive...). On Friday, Plan C was going smoothly; they had to replace the cable for the drill weight, but that didn't take too long. Saturday (day 5, if you are counting) was a beautiful day, and the drillers were looking forward to finishing a difficult job and getting us hooked back up to water. Instead, the drill weight, a 50# ball, fell from the top of the drill rig and hit the driller in the side, knocking the wings off several of his vertebrae. So he is now in the hospital, in serious pain, his daughter is looking for a driller to finish the job, and we have no idea when we will have water again. It's enough to make a monthly water bill look good.
While I was looking for some information on well drilling, I found a nice explanation of why well pumps are at the bottom instead of the top of the well.