Go through the Pros in the OP.
I don't think they apply to most cities.
I'm only "very" familiar with DEN, so I'll use that as my basis. The other places I've just "heard" about.
-Beachwood, OH is the safest Jewish community I've ever seen. You can sleep at night without every being awoken by sirens.
No sirens in DEN, but there has been a gang of people breaking into houses recently, unfortunately.-Housing is very cheap.
Same for DEN.-Parking is plentiful and traffic is nothing compared to most cities. There's also cheap train service connecting the jewish community with downtown and the airport.
No issue with parking or traffic either. A lightrail from the airport to the community is almost complete.-In University Heights and Cleveland Heights you can get $4,250 (K-8)-$5,700 (9-12) per year vouchers to use for private schools regardless of your income level.
Don't think they have these vouchers.-Free busing for kids to the Jewish Schools.
Don't have this in DEN, but the modern school is walking distance from the modern community and the Yeshivish schools are walking distance from the Yeshivish community (IINM). Modern families sometimes/often send their kids to the Yeshivish school and those kids need carpool.-The streets are clean and everyone has their own garage. There's no alternate side business and no parking meters.
Same for DEN in the community; I don't know about downtown.-Taxes are moderate, much less than NYC and LA, though more than MIA.
Property tax is insanely low; I don't know about sales tax.-Stores have generous policies compared to the NYC area.
Not sure what this means. Most stores are the same big name chains.-People are generally quite friendly and willing to help you out/midwest attitude and slower paced.
+1 to DEN.-Kids seem to come out of schools like the Academy with their heads on straight, generally not nearly as corrupt as some that I've seen come out of LA/Miami/NYC.
As I originally said, the schooling isn't great in DEN. Bais Yaakov has fantastic academics and learning, but a modern family would need to reinforce their beliefs at home and help their children not get influenced/hurt by the school's mindset and rules, if they so desire. The boys Yeshiva has subpar academics; I'm not sure about it's learning. The modern school has subpar academics and a MO-not machmir mindset.-Tons of young couples have moved to CLE in recent years due to very low cost of living, high-paying medical field jobs, and for Case Western's dental, law, business, and medical school.
Don't know about the Yeshivish community, but he modern community has seen an influx of young couples (30s with kids), however, to the more MO-not machmir Shul/school. Not sure about jobs. Downtown has many big firms and there are several hospitals in the area. There are many doctors in the modern community FWIW.-There is a rejuvenated downtown core with multiple sports teams, a plethora of museums, water activities, beaches, comedy clubs, broadway shows, a smoke-free casino, etc. Other nearby activities include the NFL, Rock and Roll, and inventors hall of fames, an emerald necklace of hiking trails and national parks, and the world's greatest roller coaster park.
MUCH BETTER football team in DEN 
, Six Flags in downtown, and plenty of museums, shows, etc. Of course, DEN's main pull is it's location just 1-2 hours away from different Rockies' options including Vail and Rocky Mountain National Park. Pretty sure DEN wins the Outdoors Award of any OOT community.-Many major cities (Baltimore, Chicago, Detroit, NYC, Toronto, etc) are within driving distance.
Definitely a negative is that it's far from the East Coast, and there are no Jewish communities within driving distance. LA is a 2 hour flight away. For someone with family in NY and no family in DEN, that can obviously be a big issue as already discussed.-Every 4 years your vote really means something.
Same for DEN.I'll add one more point: most people don't know this but DEN get appx 300 days of sunshine a year and generally is not this cold, snowy place that most people think of it as. A short drive will get you all the snow you want, but the city itself has quite nice weather. Plus, being so high above sea level means the air is always fresher.CLE is a much larger community than DEN, PHX or the options in Texas.
Just look at the schooling options, they don't compare.
I guess I'm underestimating how large CLE is. Perhaps I need to visit.
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