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

My bookkeeping firm provides me with a steady active income, which allows me to keep doing deals, cover unexpected expenses, and navigate the occasional black swan event.

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

The part of the home you live in can be covered under an HO3 (homeowner’s) policy, but the rented unit needs to be covered by a landlord or dwelling policy like a DP1 or DP2.

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

You will need to cover perc tests if needed for each lot and then hire a surveyor to draft the ANR plan for submission to the town, just treat wetlands as sacred Indian burial ground - stay away from them and your costs will be very low.  

Each lot is assessed with the taxes to cover such cost and they are paid monthly for the first 15 (give or take) years as part of your mortgage payment.

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

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

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