The roof was fixed in a temporary manner to prevent further damage and active mold.

With regular inspections, I'm not as worried about using all of the security deposit for damage, but I have had the "by the way, I'm moving and I'm using my security deposit as last month's rent" situation thrown at me, despite the lease agreement stating the contrary.As a result, I have also gone to collecting last month's rent in addition to a security deposit upon move-in.

If you are working with a more proactive PM, you probably don't need to be as concerned, but tenants should know that they are being watched and will be held accountable for damages and/or other lease compliance issues.

Once you've found a replacement tenant, you should terminate the existing lease with the current tenant, do a walk-through, return the security deposit (minus any deductions for damage as appropriate), and then sign a new lease with the new tenant and collect a new security deposit.

If you're options are preventative replacing now or replacing next year and incurring unknown other damages due to it failing, then definitely get it done before it breaks.

The house had mold damage, termite damage, water damage etc.

I don't want to get up there with my chest puffed out banging on the doors demanding rent or threat an eviction.I have seen huge damages take place on a friends property.

If you work with the right property manager, you could possibly never have to deal with an eviction or damaged property.

When the roof is kept clear of debris it's not a problem, but otherwise the situation has previously caused water damage to the ceiling (which has since been repaired).

They are seeking monetary damages and an injunction.