New developments happen because there's potential in the area a lot of times.

Regular inspections are a good way to check if furnace filters are cleaned, smoke alarms are working, etc.

But as an agent, you are a contract employee so if you are trying to buy properties and can't show consistent income, you will only push your dreams further down the line. 

Not aware of how construction cost are looking in Milwaukee, but I'd talk to a couple of contractors/developers in the area.

A detached quad consisting of four one bed one bath units will cost significantly more than an infill quad consisting of four one bed one bath units etc..Lastly, there are very few zoning districts in Philadelphia that would allow for a 4 unit building to be constructed in Philadelphia on a parcel that is only 1,000 SF and from a practical standpoint the units will be quite small when you consider the need for open area and common halls/stairs.

How do you like the phx area? 

Colorado Springs property tax seems ridiculously low compared to Austin and its surrounding areas. 

I see you are a CPA.

This would allow you to use the tax and find an area with a greater growth and cash flow potential. 

I'm currently helping an E5 engineer with a house hack in the college area out here in San Diego.