Teach implies knowledge and wisdom, I'm just telling you my opinion
Would a city+state.TV over 250,000 be worth more than a reg fee?
yes, however you may have to wait until another end user enters the market. I have not purchased every city+state.tv out there.
What if the overture is lower than a city+state that has a lower population than the one in mind?
the population + overture should both be considered. Considering a city without search results is almost as bad as a city with a small population. Some cities, like the old rust belt, have a bad rep for internet usage. So a city like Canton.TV may be above 250K, but I'm not touching it. A So Cal city with 100K like Palmdale, CA might be better than Canton because of growth and internet usage rates.
What if city+state turns out to be a long name (hard to type)?
Well the residents have to print it when sending a letter, filling out a form....for those residents, they probably have the keystrokes down.
Charleston, SC is great for internet usage. only 100K in the city.
You know a good GEO Woodbridge, VA. I don't know why; but according to my internet usage data, Woodbridge is a top 100 US City on our network.
There is another one in the Chicago area, but I forget which city.