My aim is to maximize my monthly income to supplement my retirement fund (CalSTRS) after 25 years in education, within the next five years.

We had planned to have a lawn care service doing that, but until we can get the rental income up a bit more, it would be a cash flow killer.

The fees are built into the portfolio where the sponsor earns on their spread over the actual yield to investor, so there is no decrease to capital going into the portfolio.

The units are currently occupied with tenants and is being rented for $1280 each ($2560 minus $500 HOA: $2060 Net Earnings).

House hacking is one of the most popular strategies you can take and it can be a great way to build wealth and generate passive income but it's important to have a long-term plan in place.

The way the deal would work as it stands now, he would put up about 65% of the money i'd have the rest and I will buy my way (via cashflow, and income) to 50/50.

General considerations include:Income Taxes- Report rental income, distinguishing between short-term and long-term rentals.- Utilize depreciation deductions to reduce taxable income.- Understand passive activity loss rules limiting deduction of losses from passive activities.Capital Gains Taxes- Be aware of tax implications when selling property, considering short-term and long-term rates.- Explore strategies like 1031 exchanges to defer capital gains taxes.Deductions and Expenses- Know eligible deductions: mortgage interest, property taxes, insurance, maintenance, and management fees.- Maintain detailed records of all real estate-related expenses.- Use cost segregation studies to expedite depreciation of your properties to offset large income gains.Entity Structure- Choose appropriate legal structure (LLC, partnership, or S corporation) with consideration for different tax implications.Tax Credits- Explore available credits, like energy-efficient or historic rehabilitation credits.Qualified Business Income (QBI) Deduction- Check eligibility for QBI deduction, providing up to a 20% deduction on qualified business income.Record Keeping- Keep accurate and organized records for tax compliance and audits.State and Local Taxes- Consider varying state and local tax implications, including property and income tax rates.Tax Planning- Engage in proactive tax planning, consulting with professionals for a comprehensive strategy.Tax Changes- Stay informed about changes in federal, state, and local tax laws affecting real estate investments.Remember to consult a real estate tax professional for personalized advice based on your specific situation.

Combine that with SS income (maybe?)

If you are looking to buy based on NOI (the income stream) then you should educate yourself about cap rates.  

So it’s all tax free income.