How can I prevent this?

As an OOS owner, I don’t know how to (100%) prevent such things from happening.

Quote from @Brandon Allenczy: I try to prevent situations like this because they become revolving doors and you lose control over who resides there.The most I would do is add the new tenant for six months.

preventative maintenance, new a/c systems, new water heaters, raising rents Lessons learned?

@Tom Gimer, @Kevin SobiloIs there any way to prevent @Matt James' predicament in the future?

Estimate today's cost to replace that element (should be easy if new construction, more difficult to develop an accurate number for an older property, but absolutely do-able ), divide by number of years expected life, set aside that much each year until item is actually scheduled for replacement, adjusting the "remaining life" annually for accelerated deterioration or prolonged life due to well planned and executed preventative maintenance.

Definitely trim it to prevent damage, but the tree may provide value......?

Purchasing a property in the San Bernadino mountains.Will need a retaining wall built to prevent soil erosion.What sort of costs and planning should I expect with this type of project.

Similar to the lock on your door and security system in your house; the goal is not to prevent the hack but make it less enticing to attack you versus someone else.

If you say spent $100k now would that prevent you from growing that say into $1mil in the years to come to prevent you from doing “whatever?”