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We are on septic and well, have been for 9 years at least. It isn't the issue that you think it is, sure there is more to think about than just hooking up to the city, but I'm ok with using whatever water I want without paying for it...which I would have to do if I hooked up to the city sewer and water. I know the cost is not a concern to you though, but in the long run you might start to complain, so don't entirely discount this.
Plus, the taste is honestly night and day difference, well water tastes much better. Get a reverse osmosis system installed and it will be some of the cleaner water you drink (healthier than all that chlorine the city puts in too).
We got a generator for reasons other than worries about the septic because unless your power is out for days, it isn't going to be an issue, but it is still nice having a generator that powers the whole house including the water system. Not needed if you aren't in an area where the power goes down frequently, but the generator is just convenience more than anything else.
Honestly, I get the tank pumped every 3-5 years, and I change the filters on the reverse osmosis every year (and probably replace the UV bulb about 3 times a year, but the filters and bulb are easy). If I drive my truck on the lawn I'll go around the leeching field but that was only when I was building a zipline structure, now there is nothing I need to worry about that is heavy going on the yard.
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