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.

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

The portfolio covers itself.

Cancer/heart need to fly home.Over the course of this post will cover the following Real Estate angles. 

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.

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.  

If the water bill is $100 a month, increase the price by 20% (or whatever you decide is fair) to compensate you for the time required to split and bill and to cover additional use when tenants squander the utility.

Thankfully, my wife is still working, and we have a few months’ worth of emergency funds to cover our expenses.

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

Does he not cover that yet?