If you can get a few roofers (not handymen) out there to assess the situation, they could probably give you some options that would be tailored to your specific roof & circumstances.

@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.

I have a tenant who often doesn’t even initiate the payment until the grace period, which results in frequent payments arriving well beyond the grace period.She owe back rent as well plus other late fees, but I’m interested in submitting a comprehensive tally for the eviction process, so I’m looking for the legal definition in CA. 

In your assessment, is the carpet in good condition? 

It often requires a comprehensive review of all your policies, coverage gaps, and potential overlaps. 

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.