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.  

Target cheap BRRR and Manufactured homes, use these to provide a basis for me to get into new construct multi-family (4-Plex), and BRRR Multi Family, I will enter these into the market as the supplement to the mid level and place them on the side of my small city that is most adjacent to the big city, to try and tap into the people in the affluent part of the city.

Most people don't have the cash to supplement from somewhere so they end up replacing all debt. 

If you need the LLC, let the LLC supplement your insurance, not replace it.