I have a property manager who inspects before and after a renter's stay. I obviously pay for that service, but it is well worth it. If there are problems, they are itemized and I either keep all the deposit or what is needed to cover the damage. I also have a clause in my contract requiring the renter to pay for any damage above and beyond what security deposit would cover. But to recover this, you would have to go to small claims court which may or may not be worth the hassle depending upon the damage. Only once did I encounter that bad a problem and I actually posted about it on TUG last summer. I never did recover all the funds needed to rectify the situation, but it was from that incident that I learned to increase my security from $100 to $250. Hopefully, that will be sufficient.
If you a renting out a timeshare week, it would be a very different situation. When I rent out my TS, I do not collect security - the TS management takes care of all that at the time of their check-in and I have nothing to do with that.
Hope this helps to answer some of your questions.