At What Point Can I short sale a property?

Is is possible to short sale a house that is not in trouble or late on payments?

Unlikely, since the lender will want proof of the seller’s hardship. If they are making payments on time, the lender assumes all is well.

Yes, If you can show and prove to a lender that the property is in immanent default they will short sale.

I have done 2 this year alone.