@Cody M.I would add a Phase I Environmental Site Assessment as a contingency to any offers on properties more susceptible to environmental issues (dry cleaners, gas stations, auto repair garages, etc.)

Current owner is asking WAY too much (2.5 assessment), and they do Airbnb with it. 

Make use of tools like PropStream or Zillow’s market analysis feature to assess property values and rental potential.PS: Did you know that Indiana has one of the lowest property tax rates in the country, making it a relatively cash-flow-friendly market for new investors?

It’s smart to research the area's saturation on STR platforms to assess competition, pricing, and occupancy rates.

In your assessment, is the carpet in good condition? 

A condo HOA can decide they want to replace all the roofs, but if the bank account is low, hit you with a $5,000 special assessment.

We negotiated a favorable deal by assessing the needed renovations and offering $60,000 to secure it quickly.

I would be on the lookout for the current condition of the units and building while you're walking through to assess how well it's maintained.

To do this, divide the cost based on the ratio of the fair market value (FMV) of each asset to the total FMV of the entire property at the time of purchase.If you are uncertain about the FMVs of the land and the buildings, you can alternatively allocate the cost based on their assessed values for property tax purposes.Source: IRS Publication 527 (Residential Rental Property)

Buy a few leads—start with a small test amount—and assess their quality for yourself.