Sole proprietors: few questions for those who are savvy about $ and taxes

I've been bitten by the savings bug and want to overcharge the possibilities of my earning potential.

I currently max out both my Roth IRA and 401k annually.

I'm considering having side-gigs that would make me a type of independent contractor, and somehow give me tax benefits. I want to save money like the wealthy and the loopholes.

-Job 1: type of mentor job that will pay a stipend -Job 2: mobile notary -Job 3: real estate agent

Idea: the side-gigs will not exceed $15k annually since it will really be part time, during summer months or holidays.

What will benefit me the most? A SIMPLE IRA? SEP IRA? SOLO 401k? This will be with Vanguard, as they have all of my other accounts.

Will fully funding my work 401k and Roth IRA conflict with the funding of money from the side jobs?

Can I put all of the income from those jobs into an account without taking a paycheck?

Can I deduct the expenses from those jobs on my personal taxes?

Will a self-employment tax be imposed on me?

Thank you so much for your time and knowledge.


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