The feedback here is to assess if this Open spaces program is worth the $8000 investment.

the house has a bunch of equity, being worth about 750k when fixed up.I  know that on a standard convenetional mortagage foreclosure, there usually additional fees such as unpaid interest, attorney fees etc, apart of the princiapl balance.Is there a way to conservatively assess what will be the actuall "Pay-off" on the 1st?

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.

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.

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