I've handled several condo water losses from sprinkler system malfunctions. 

The two hardest things on a property: water going where is shouldn't be going and a tenant trying to do their own handyman work.Our rental agreement clearly states what we will do to maintain our property, what the tenant must do to take care of our property, what to do if something gets damaged or malfunctions, what to do in an emergency, how to contact us, how to place a service request, what to do if a crime occurs on the property, insurance requirements (ours and theirs), and who pays for damages.

I've spent about $1,500 in average the last two years (0 this year so far) due to a termite infestation and my A/C unit was malfunctioning.

Would a roof repair or a single system malfunction and replacement put you in serious negative territory?

Your lock malfunctioned and someone broke in. 

My two cents to your issue would be to analyze the roof from the point that you know it is malfunctioning: the fasteners.

Our realtor also found a septic inspection report from earlier this year that says the septic was showing signs of malfunctioning.

I don't have STR but if I did what I'd consider is:Do competitors have it and is it the difference between them selecting my unit vs theirsIf the playstation decides to malfunction during their stay are they going to write you a negative review for it or call you asking for one that workWhat if they put one of their own games or a redbox in, it gets damaged, are they going to ask you to reimburse themHow many bad #&@ kids or drunk adults are likely to break this playstation and act like they don't know what happenedCould the money you spend on the playstation and games be spent on something more attractive (larger tv or more TV's)I think that's my long way of saying no. 

But the detention pond could malfunction and overflow, flooding the nearby houses...

It's not my fault my lease just so happens to end in March and the meters were malfunctioning.