I try to have my renters meet each other or at least have a phone conversation to make sure they're compatible, but even then, you just never know if they will be.

Dumb question, but is asking a police officer to swing by just to assess if there is weed (quick smell test) be too much/a violation of anything/asking for trouble?

I would bring in a drafter or architect to assess it and see if you only need the building plans and pay permits: Building plans about $3k to $4k since everything is done... and city permits about $4k to $7k and make sure that you don't have to do anything major... front foundation could easily be $5k or more plus engineering work and stamp. : so, assess all systems and see for obvious things like : garage door, ceiling height, perimeter foundation and drainage, framing if you can, attic space, electrical, plumbing etc 4.

After assessing the property's value and market conditions, we confidently made a competitive cash offer of $180,000.

If you believe the new assessment is too high, you can file an appeal.

You'll want to talk to a local probate attorney to see how much time that could take.If the squatter is not making mortgage payments, you've got perhaps another month or two before the lender begins foreclosure proceedings.In your situation, I would approach the squatter to see inside the property to assess the condition.

Definitely make those assessments during inspection or prior to making an offer if you can to save yourself the time. 

@Joel Florian Your assessment of Roofstock is pretty accurate.

The deal was contingent upon 60 day due diligence and a clean Phase 1 environmental assessment.

However; investors also bear a responsibility to sufficiently investigate the contemplated investment, to assess whether the investment is appropriate for them, and to know or learn enough about personal finance to evaluate whether or not they are able to sustain a loss without undo strain.