@Todd Nagel - For sure. It's not all doom and gloom. I bought a 4 plex there in the beginning of the year, so obviously I think it's a worthwhile market. But, as you said, yes, you need to know it. People have absolutely lost their shirts there and I don't want to be one of them.
For instance, I have HOURS of video of me just driving up and down streets at different times of day and week making verbal notes about where I am and what I'm seeing. I also leaned heavily on others for real day to day experience. I usually gut check what I think I'm seeing with my realtor and some people who are familiar with the area. My tenants have offered lots of opinions about parts of the city they like and they don't (and I've often driven to the areas to determine if they were right). After all of that, there are only a few slim areas I'm running numbers, just because I know them well enough to feel comfortable and there are enough deals that I can be that picky.
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@Joshua Zapin - One of the reasons I like Pueblo is that it has (had?) a lot of growth engines for such a small town.
One of the more interesting in the area is that people are selling in the Denver area and moving down to Pueblo West where they can build brand new for less than they sold for and still keep a nest egg around. That seems to be attracting empty nesters and the like. While that alone is pretty good, it also fuels healthcare in Pueblo (proper) and secondary services like restaurants and the like. It's also worth noting that Pueblo's hospital system has a pretty decent feed zone between highway 50 (east/west) and southern I-25. You can see the impact this is having on northern Pueblo near the hospital where it is gentrifying (quickly). Also, north and north-west Pueblo is very nice (near Pueblo West), as you can see on the map @Sam Dangremond shared.
Another is CSU-Pueblo. Belmont (and especially the stuff right next to the campus) are pretty nice. They definitely are drafting some of the money coming in there - between student housing and staff housing as well. Aside from the college, there is a lot nearby that is attractive (eating, shopping, etc), etc. Walmart, target, and home depot are all nearby over here.
There are definitely some people who are commuting to Colorado Springs from Pueblo, one of my inherited tenants was one. I think that as prices go up in the Springs and the supply keeps being strained that will be the case. It doesn't hurt, but I don't think I would count on this as what keeps the economy humming.
There are also a handful of other primary industries around. There is a steel mill that has been around forever. In spite of its reputation it's actually only something like 700 jobs. It is no longer the largest employer in town even though Pueblo's website said it was as recently as last year. Trane (Nothing stops a Trane) has manufacturing in the area. There's even farming - pueblo is locally known for its chiles throughout southern Colorado (and yes, they are pretty good). There's even a pretty reputable water filter company down there, I hear.
Like I said earlier, I think Pueblo is going to get hurt more than Denver and Colorado Springs, only because, even though it has a lot of primary industries, they are less recession resistant than are available up north (I mean, Denver has the state capital and Politics are always in season, it seems). However, it's hopefully less boom-bust as it was in the past when steel was it's life-blood.
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After all that said, as @Rick Wade said, I think it is tricky too. There's a lot going on and its not as easy to find some services as you might in larger cities up north on I-25. Honestly, I personally like that too because it's a barrier to entry. Once you find people you trust, you have an unfair advantage. I'm not sure if that's what he's referring to, but that's been the tricky part of my experience.