The water heaters are in tight crawl spaces which I dislike, it's got swamp coolers which I dislike, and pretty much all the other work that needs doing just doesn't look enjoyable and I'm already too busy.

We come up here every year, and it's always cooler than New York City, but this year is especially great.  

Mechanicals: hard to check AC in cooler weather, but drop AC 10 degrees before house temp and check it.

http://easyrentaltools.com/tutorials/depreciation-calculator-1.cfm

And to make it even cooler - I'm actually going to be doing the analysis of an actual property I just got under contract today!

I was thinking of moving there, up on the hill in the Center as it is 10 degrees cooler at night compared to the sweltering Heat we suffer with here in Tampa.

Yes, we are in the South, however there is likely a slow-down during the cooler months of late Nov-February. 

That doesn't include converting from swamp cooler to AC, at another $6k cash.

Moving air makes you feel cooler than you really are.

If you choose to live in the Phoenix Metro area, you're an hour outside of Prescott (cooler weather), only 5-6 hours from the beach (Cali), and not to mention all the amazing restaurants there are scattered through out the valley.