Bad news you may also have to cover your own commissions. 

If their policy ever lapses or is canceled, they are automatically enrolled in my master policy and covered. 

Since you only have 2 full time and two part time staff, who covers their vacations and sick time?   

I think #2 covers 90% of the work, BUT there are people whose debts are out of line with their income.

With the situation you're going through, your first thought was likely "I'll raise the rents to cover this." 

The main factor is will rents cover the debt liability and can you sustain 3-4 months of no income to cover the debt? 

The scope of what you asked covers a broad area from estate planning, to tax planning and forward. 

The projected rental income wouldn't cover the mortgage and HOA at this time.

STR management is 20-25% (I would recommend self managing or getting a VA), since income is higher you could probably get away with 5% for maintenance / cap ex but remember you need to cover utilities and cleaning for these units which drives up costs.

That covered pretty much everything!