As you said, worst case scenario I'd only be out $500 for the inspection so it's not the end of the world.

But this has been the worst closing of my young investing career.  

I do applicants one at a time if there are multiple adults (I have them to start with the "worst" one).

Maybe I'm just finding excuses but I tend to always plan for worst case scenario which might not be wise when it's time to take a little risk.

Make sure they give the worst case longest timeline.With all of this information you now need to contact the bank or whoever is holding the Note on the property to talk with them about what is going on and next steps.

I think one goes into a deal thinking the worst case scenario is that they profit 10-15k, but never that being the best case scenario.

In a market where properties are selling at 100% - 105% of asking with multiple offers (and assuming the property is properly priced), know that the lower you go below that range, the worse the chances of your offer being accepted.Run the numbers on the property, assuming the worst. 

If you're serious about getting a good deal on a primary, stick to your guns and make the ask.The worst they can say is 'no.'

@Igor Nastaskin Chase is the problem here...everyone is more conservative, they are of the worst...send a DM

You still have equity in the house (because you put 20% down in the first place), and (worst case) you can still sell it and walk away without going into foreclosure.