W2 or 1099: Working with my father

Hello everyone,

So I am 26 years old, single, no dependents. I quit my first job last month to work with my father in his small business (it is an LLC and only himself works in the business as of now). I was in a prior company for 2 years working as a W2 employee. I got health care, 401k, and other benefits there.

I am now working with my father because he started getting a ton of business and the family company is growing. We agreed on a salary of $70,000 USD/yr for myself. I also have a second job (part-time with W2) as a University lecturer where I make $19,000/yr teaching just one class per semester. My father will NOT give me neither healthcare nor 401k (No benefits).

The whole point of me going the W2 route was because I’ve been looking forward to buying a home, but I live in a HCOL and right now it’s impossible to compete in the housing market as a first time home buyer, I also don’t have enough cash for a down payment and apparently you need to wait 1-2 years after being employed by a family member. So I thought that perhaps being a 1099 was best as it would allow me to save the most money and be able to go into an investment venture my dad is doing right now which I don’t need as much money, but I still need to save.

All in all, I don’t know what to do because if I’m a W2 I have to be on top of my father to send the taxes every 3 months, and he is quite disorganized, I’m concerned I will end up getting fucked because of his lack of attentiveness. He doesn’t even have a payroll system so he pays me through Zelle as of now… I don’t know if I should create an LLC and pay myself through it and keep the receipts of things and use it for taxes? I don’t know how it all works, I’ve never had to think too deeply about taxes before.

Thanks for your help

Edit: I’d like to add that I am asking for advice and for a pro/con conversation as I’m not too sure which is best for me.