@Christopher John McCarthy Since you are open to moving and want to house hack, I would suggest moving to a place you want to be. For your own personal happiness - life is for enjoying. For example, it appears for @James Carlsonlegal marijuana is an important factor to consider ;) It is pretty subjective and hard to give advice on.
But there are some objective things you can consider too. Sounds like you prefer a growth market based on the cities you mentioned.
But what creates growth? Population. But people need jobs, so you also want job growth. And you want that job growth to be in good jobs, that push up income, so people can afford to pay more for housing (driving appreciation). That is the demand side.
I put a chart together to compare this demand 2010-2019 using Census data. What you'll see is Chicago has had no population growth and very little job growth compared to the others. And to be expected the income growth is also less. The black dot is the median income in 2019, and although pretty high for Chicago, given these metrics does it seems reasonable for the income to keep climbing? For rents and housing prices to appreciate? Doesn't seem likely to me.
What about demand side? Austin, Colorado Springs, and Denver permitting seems to be keeping up with population growth. Chicago is still permitting a little, even though there is no population growth. Phoenix looks like there could be a delta between population growth and permitting, suggesting more supply side shortages compared to the others, but this could also be do to over-building prior to the great recession.
In attempt to look at supply side from another vantage point, I looked at how many households are being formed, vs housing units being created, from 2010-2019 and took the average (otherwise the graph is all jittery and hard to look at). In Phoenix, households are forming faster than units are being created. Now, you can't actually form households without housing units, so I think this just suggests Phoenix is consuming its previous oversupply. But still, that's a good thing.
How might the cities fair in the future, given the economic turmoil caused by COVID. Here is another vantage point of total job growth over time, paying attention to job loss/recovery in 2020. Chicago has petered out since about 2016, and COVID erased all job gains since 2010. Austin has rebounded the best. The others have faired comparatively decent.
Lastly, an important metric is rental yield (the 1% rule). How likely are you to cash flow in these markets, vs feeding the beast? I have plotted below yearly rent / house value, as provided from Zillow data. Chicago smashes all others out of the park, and that may be important to you if you seek cashflow. However if you are looking for growth, well it's no surprising the others are a lot less. One thing to consider is that both Chicago and Austin looks better than they are, due to high property taxes (which eats into your cashflow, which isn't captured in rental yield). And all yields are going down due to the current housing craze.
Data is useless if you can't make a decision based off of it. For me, and to meet my goals, I like Colorado Springs. It swings with the heavy weights, but isn't a massive beast of a city like Phoenix. It has a better rental yield than Denver with an easier entry point, and therefore better runway for appreciation. And maybe some of that Denver growth will spill over and give tailwinds to Colorado Springs (though it is doing just fine on its own accord).
Disclaimer: I don't yet invest in Colorado Springs, but with analysis such as I have outlined above, I have chosen it as my target market.