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.

No, I will continue to work at my current job and use this as supplemental income. 

I have recently quit my job working for the government  and decided to start investing to supplement the income I have just walked away from mainly from rental properties.

It’s very simple and inexpensive to add that “special assessment” coverage to supplement the HOA’s policy. 

If she is now in a condo her best option is to move to an apartment and use whatever monies she gets from the sale of the condo and use it to supplement her income to pay rent.This would be the best option for you as well.

This won't be a supplement to your other incomes...it will take it over.20-30 properties will need to be paid for with all cash since it will be very difficult (spelled "impossible) to get traditional loans due to the low cost of the properties. 

Once I am retirement age these properties would be paid in full and the rent would supplement my retirement. 

I expect to get $4,444 in compensation, which I plan to put towards my 5% downpayment and supplement the remainder with cash.