I then want to compare this to the median home price by bedroom count in each market.

Primary reason is that it's not economical to building in today's market compared to a larger industrial building with only 1-2 tenants to manage instead of 30 smaller ones.

Pueblo's housing cost on average compared to Colorado Springs is $150,000 less. 

However, the new Community Development Grant (CDG) program simplifies access to critical funds, offering three distinct grant categories:-Small Grants (up to $250,000)-Medium Grants ($300,001 to $5 million)-Large Grants (over $5 million)These grants can support a wide range of projects, including office, retail, cultural, industrial, and mixed-use developments of more than 10+ housing units with ground-floor retail.

So, given you are in a lower end area with lower rents, you need to reserve more money on repairs, maintenance and capex compared to a higher rent area, since that $200 HVAC or plumbing service call is 25% of $800/mo, but 10% of $2,000/mo.  

The issue in Chicago is our unique 2-4 unit inventory that is still more approachable in price compared to other big city markets.

Solo 401k plans are often quicker to setup and cost less money over time compared to most self-directed IRAs.If either the IRA or 401k are to obtain financing for a purchase, a non-recourse loan is required.

It might rent for $800, but the rehab costs would be so high compared to it's ARV. 

Even with the equity built up on my current property it would not be enough to put 20% down on something comparable.

The waterfront properties along the Chesapeake Bay and Potomac River have higher demand and can command premium prices.In recent years, housing prices in Southern Maryland have been steadily rising, but at a slower rate compared to the DC metro area.