Hey Joseph - Like you, I use TurboTenant, supplemented with other platforms and customized spreadsheets, integrated through some automation and delegation.They're rolling out a more robust maintenance portal which should save you some headaches too.

@Kao Lor There are no regulations in Winston Salem, my wife and I own two MTRs (and we're planning on converting our other LTRs over)- helped my parents purchase, set up and get one going (to supplement their retirement) and my bother-in-law purchased a property and got one going here as well after he saw how well ours are doing.

My SSDI is my only income, and my disability prevents me from working to supplement it. 

I am looking at similar size single family homes in the north west area around 250k… essentially I am just trying to get a grasp of what to expect year one- if there is actually some profit to be made and supplement or if is more likely to be near a wash.

Tell you insurance company you need to make a supplement from the damage caused by that claim and they will tell you if you are within your window of time to do so

Do I think they need to supplement it with something that drives more immediate results?

You could consider getting an umbrella insurance for greater protection in supplement to your primary liability insurance coverage.

Additional Income: The most obvious of the benefits listed, ADUs can supplement the mortgage, offset living expenses, or even pay for your next vacation!

We are primarily long term buy and hold investors looking to supplement our retirement income.  5 properties in 3 years is awesome.

Therefore, I’m jus looking to supplement at the current moment since I’m fresh.