I hate that well guys are so unreliable these days. But it is not just well guys, every profession is having the same problem. I can't get anyone qualified to work on my car, fix my refrigerator, or AC unit. Too many people with college degrees they think makes them too qualified to get their hands dirty, so they just don't have a job. You just can't get good help with anything these days, which is why DIY forums are popular. At the house I live in now, I made the mistake of paying the plumber all but the last 5K and he would not show up and finish the job. No other plumber would come over and finish the job either. The plumber broke out concrete from both showers and moved the drain pipe a couple of times because he couldn't get them in the right place. My shower floors are weak feeling because of this. Then he just would not show back up and finish the job. I had to install all the fixtures and appliances myself. So, plumbers are not any better than well guys.
I hate to talk bad about government officials, because there are some out there who are actually trying to do good for the public. But counting on city water means counting on city officials to know what they are doing. Unfortunately many government employees are such because they couldn't make it in the private sector, or want a job where they cannot be fired even for being incompetent.
A proper well uses a pitless adapter and has all the pipes underground as well. No worries about freezing, wasp nest, etc. Luck doesn't have much to do with making a pump system last, except for maybe the occasional lightning strike.. Just eliminate the cycling like when using a Cycle Stop Valve and the pump will last a long time. You will also never wear out a pressure switch, check valve, bladder tank, etc.
Many hand pumps WILL work with a deep well. Gonna have a generator anyway, even without a well, as I don't trust anyone else to supply power when it is really needed. Many people just want to pay someone else to take care of everything for them. I am not that kind of person. And that 40 bucks a month for water easily turns into 200-300 bucks a month for water if you have a small yard or garden. With a small farm and animals I would not be able to afford city water. And yes a Cycle Stop Valve can make a pump system deliver water at even stronger pressure than a city water supply.