Compliance items such as adding smoke detectors, hand rails, fire resistant garage entry-door and new stairs outside.

I don't think you are going to be able to get insurance for two separate living units in a single-family when they are both illegal and likely do not have the correct egress windows (basement) for fire safety which could subject you to huge liability if something happens to either party.

Going at it a lone for the first few properties is feasible but it is trail by fire.

I left the meeting on FIRE to start implementing. 

Death, divorce, fire, home sale, floods,layoffs, etc.

Getting that first deal under my belt with the help of a mentor would significantly accelerate the process and build my confidence.I’m a firm believer in learning by doing—trial by fire, making mistakes, and growing from them.

Quote from @Francois Navarre: I have Obie for one of my rental properties affected by fires in Palisades.

I just keep my head down and fire back.

I am managing those and feel like I have been drinking from a fire hose. 

(NY counties are generally quite expensive)Do you have home owners insurance to cover fire or other damage?