It’s been estimated by one attorney I spoke with that an eviction in Cook County would take about 6 months.

@Alec DresslerYou’re on the right track using tools like AirDNA, but for better data, consider the paid version or platforms like Mashvisor for detailed rental analytics.

Reach out to me if you want their details or help with anything.  

One thing that could really help is creating a detailed scope of work before committing.

These methods include: Detailed Engineering Cost ApproachDetailed Engineering Cost Estimate ApproachSurvey or Letter ApproachResidual Estimation ApproachSampling or Modeling ApproachExperience or “Rule of Thumb” ApproachIt’s important to understand the differences between the approaches including which one best fits your property and the reliability of each approach.DETAILED ENGINEERING COST APPROACHThis approach compiles the costs from construction and accounting reports to build a report.

I’ll add a few more details and answer some questions.

We estimate the project will take less than 3 months to complete.I’m exploring alternative short-term financing solutions and would appreciate any advice or recommendations on options that might work well for this type of project.Thank you in advance for your insights and assistance!

So the question becomes based on their individual and personal tax situation what is the estimated tax burden they'd save? 

I assume something like this is more than you want to tackle for a 1st quadplex (https://www.realtor.com/realestateandhomes-detail/241-W-King...), but what about this SF for a BRRR (https://www.realtor.com/realestateandhomes-detail/2101-Arapa...)? 

Quote from @Aaron Wolman: I would call the companies (gas/water/electric) to get estimates, or an estimator out there.