Get a quote from a local roofer or two on what they would charge to replace the roof and run the difference between replacement costs and insurance costs.

Must have been nice :P To qualify for the status there are two tests: 1. spend 750 hours in a real property trade or business, AND spend more then half your working time in it.

Learn about fire suppression systems, door heights/widths, ADA, sidewalk parking, hvac, etc.Figure out how to bring value to the transaction.  

For $1,000 I will be adding a door to both the 2nd living rooms (one in each unit) turning it from two 2 beds into two 3 beds.

Prior to thinking about a rent reduction, wait two to four weeks, keep an eye on local rental costs, and interest rates.

They do not answer their phones or emails and have chosen to keep the doors closed to the public after Covid.  

I spent 5 years on the ground in the Detroit area building relationships, learning the market, etc.So you really have two paths.

I would probably post a notice on the door in case someone comes back and after 10 days assume nobody will.

Upgraded windows, landscape work and made two separate dwelling units.

@Paul Baldwin - I have found there are two ways to understand/learn something....find someone who already knows or teach/learn yourself...the later works, but just takes longer and often has room for more errors.There's no true cheat sheet until you have done enough projects in your specific area!