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Do the no-brainers first
This post on Facebook is worth repeating:
It would be smart to split the city's planned annexation into phases instead of one big lump. Some of it makes sense, and by that I mean the "islands" of unincorporated areas within the city.
Those areas are consistently ignored when roads need plowed. I have seen it myself and personally driven on those neglected streets. Just from a public safety perspective, it makes sense.
So why not do the "no brainers" first, instead of one omnibus annexation plan?
Of course, the unincorporated islands won't pay as much in property taxes. This was always about greed.