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Two people have already given you the answer to your question: One or more repeaters, possibly connected together using simplex links. This will give you wide-area coverage without the need for iffy message relaying. A single well placed repeater could easily cover 300 to 400 square miles. Motorola GR1225s are available for around $500 (make sure the finals are good) and MTR2000s for not much more. Personally, I'd go with the MTR2000. You can also build your own out of a pair of half decent HTs. If you do decide to build out a repeater network DO NOT BUY THE MIDLAND RADIOS. They only do narrow-band and for best performance, you will want to take advantage of the GMRS rules and use wide-band for your repeaters.

I don't know where the FCC is on enforcement but here in Racine Wisconsin the WI DOJ has been knocking on doors looking for the people that have been connecting radios to the statewide P25 trunking system known as WISCOM. I know 2 ex law enforcement offices that both got visits yesterday. With the visits came lots of questions about one person... All I have to say is play stupid games win stupid prizes, FCC won't investigate so here comes the DOJ. When caught these guys will wish it was the FCC because the DOJ will issue you and anal probing the likes of an alien abduction....

Morse code not needed, Ohm's law: I=V/R. Here, done, you're ready for the test. Me and later my daughter used hamexam.org for the preparation. If you create an account there it'll keep your statistics, showing the areas to study/memorize more.

Since Amateur Radio is officially designated as a service (Part97) by the FCC I cannot imagine your city is using the term with any generality. I see two options: A) talk to the city anyway and see what they say. or get a Tech HAM license, build your tower and mount a GMRS antenna on it. You wouldn't ever have to own a single piece of HAM equipment. BTW, the downside of asking first is once they have officially said no, you are totally out of luck. I suggest you go with plan "B."

Take a look, or listen, at https://goughlui.com/legacy/soundsofhf/index.htm