However, I have a $1000 deductible so insurance isn't giving me anything for the incident.

Things escalated with an incident that I will not describe in detail here, as it would take too long and nobody would believe me.

There have been multiple incidences of squatters and drug activity in the house.

Had an incident recent whereby a tenant, who possessed a handgun, used it in an altercation at a property I own.

I feel this will be a safe choice because the first one will be generating about 1200/m and facing any vacancies or unexpected incidents that could be very helpful.

Third, have the lease cover any 'pool-related' incidents. 

Now that it has been over a year since this incident with no news from the ex-tenant, I am considering to work either through a Collection Agency or a Law Firm to collect the owed money.

We permanently lost a few tenants from the incident and waited nearly 3 months for the insurance company to agree on repairs and the materials that could be used to replace things thus delaying getting the units lease and show ready. 

I need to break a tenants lease after an incident where the front door was damaged in addition to noise and disruption to the other tenant.

Then send your tenant a written warning that one more incident will result in termination of their lease.