In theory the 2nd person could earn an income but I am unsure if they would ,and if they did would any of the funds get put towards the living expenses??.
Personally I am a stand on your own two feet kind of person so I'd rather take matters into my own hands and deal with it...even if it means I have to bust my butt in doign so....at least i know it's done.
Honestly, with your rent - and it sounds like you are fulling supporting person #2? You will have a very hard time ever getting ahead. Of course it depends on your relationship with person#2. Will you be supporting them long term? Into retirement?
If you are supporting person#2 and you are unsure if they could earn an income, and you feel you have to "stand on your own two feet" and are not being supported it doesn't sound like a very healthy or mutually beneficial relationship.
Also, if person #2 can't work, and it is an option you might want to look into some sort of public programs or subsidies that could help, either with financial, social or even career counseling assistance.
I don't know what your "Family Investment $140 (somethign we are all in on)" is but you probably need to stop it, you can't afford it.