In planning to sell the final bed and breakfast 5 years ago I bought a duplex.

Both were difficult and could have been avoided if we had had better planning.

You just need to make sure when something goes sideways cause it will that you have your reserves and a plan. 

It's just about having the right team in place where you can identify them and get offers submitted quickly and solid contractors that can give you realistic quotes so your financial forecasts are accurate. 

I know that in single families in Cleveland Heights people have put in basement bedrooms with an egress window and they were on formal plans that were submitted to the city and approved. 

Reach out to your local land use planning and/or zoning department.

If you got the first house for a song and a dance it would probably be better financially just because you're getting a better price on the skeleton than you would in a fresh build.

I plan on house hacking and was wondering if I should open a new bank account solely for the rental property transactions.

Hurricane prep and Evac plan for all properties.

I’d maybe start with, I agree with $x amount even though you missed the deadline but expect the rest returned to me within x days, or I plan to contact tenants rights group to help me seek all damages allowed.