In general, government will set the assessed value lower than market value at reassessment in order to neutralize appeals.

I would like to find a way to generate additional income and am exploring options other than having a long-term roommate.

Real estate agents, property managers, and contractors who specialize in your target market can save you time and money in the long run.

In general I have unfortunately never gotten much return on any social media marketing. 

It may take 1-2 years and by the end you will have forced some appreciation from the renovations but also got some natural appreciation from the market.

I am in the Milwaukee market. 

In southern CA, even garage conversion ADU additions are typically costing more than the value added.  

Texas has additional laws against these options.

Quote from @Brendan Jones: For the homes, and or properties that you will use as a primary or a rental property one big thing I look for is infrastructure in the area, extrinsic value (I.e. hospitals in the area, schools, and job market), and the last thing is creature comforts for people (I.e. is a store to get groceries 1 hour away or 2 minutes away).

It’s a market where cash flow is achievable without needing a massive upfront investment.