It was during the whole underwriting process.

I have found a contractor I trust should any repairs be needed, secured a cheap month-to-month rental in the area I will be looking for when I start my search in April 2024, and am in the process of interviewing lenders recommended by BP and friends who own property in the area.

If you're planning on taking STRs seriously to maximize cashflow, I would take the time up front to either 1. hire a professional to handhold you through the process or 2. join a mastermind.

Landlord-friendly states generally have laws and regulations that are more favorable to landlords in terms of property rights, eviction processes, and other landlord-tenant matters.

If you decide to let your roommates know that you are the landlord, I would also recommend handling the leasing process instead of using an agent to be very clear up front that you are the landlord and roommate of the prospective applicants. 

To help you get started, I recommend implementing a thorough screening process for your tenants.

Full process control start to finish.

Some insurance companies have told me they don't insure LNC buildings cause 'replacement' wouldn't be a straightforward process, as there's usually no detailed record of such grandfathered buildings' layouts in the records to permit re-building following a fire, flood, quake, etc.Others have said at least in while securing quotes, it's a non-issue.Surely they both can't be correct!?

I am also personally looking to buy in a city like Detroit to learn the process.

Their thought process is that eventually interest will go down and home prices will spike up!