We have always had our security deposit at $1,500 and hasn't been a problem since we started this year (8+ rentals thus far); I just recently increased it to $2,500 because of our No. 7th renter who had an accident.
This experience was the first time that I had to take the entire deposit which didn't even come close to covering the damages. OUTDOORSY isn't doing such a great job with communication when it comes to dealing with the claims folks. They only respond via email, never a call back number and I keep getting canned email responses which are always bad news about what isn't covered by the insurance coverage.
This one rental (No. 7) has been pretty frustrating; I just found out today that renter No. 7 did have a police report which was associated with the accident (backed over a mailbox). After reading the police report, it turns out that our AIRSTREAM had to be pulled out of a ditch; that explains all of the undercarriage damage.
So in short; I'm holding at $2,500 and to be honest, it still may not be enough to cover damage from something as simple as backing over a mailbox.