The type of your business or the fact that you are paying them as an individual does not take away the requirement to file 1099s." 

Use individual leases to reduce risk, screen tenants carefully, and set clear rules about noise and responsibilities.Good luck!

Are utilities paid by individual unit tenants?

Our best use for the property would be to build a couple of large estate home (8k sq' and up) and form a private estate, but, being that we are in the County with no existing zoning requirements, we could also build what we want and potentially turn it into an income generating property.

If I did my math correctly, on a 3,600 SF triplex where you buy the land for $150k, you generate a gross profit of about $84k (based on a $140/sf build cost and sale price of $205/sf), before you pay interest on any borrowed funds or closing/commission costs.

Start with your primary, rent out any spare bedrooms "house hack"Use that to practice upgrades, kitchen, bathroom, curb appeal... etcNow you have experience as a landlord and flipper, use that to buy a distressed propertyAdd 40% equity to the property through home makeover, refinance into a low cost mortgageNow you are cashflowing a healthy margin on a second property, use that to build equity over time, cashout later and buy your duplex/quad.If it's going to take you 10 years to save up a down payment for a small apartment building, yeah it makes more sense to start growing your portfolio with cheap SFR flips instead.Every market is different, every borrower is different, every property is different, it would be ill-advised to recommend anything without recognizing the individual's nuanced goals and objectives with their next acquisition.

.- The reality is this depends on each individual caseworker.

Owner-occupying a small multi-family property is a smart move—you're reducing your own housing costs while building equity and generating rental income.

It allows for a period of adjustment during down periods and takes advantage of the market's upward trajectory.By projecting returns, considering a solid five-year window, timing the market strategically, and analyzing historical patterns, I've been able to make profitable investments and build lasting wealth.Let me share with you the strategies on creating generational wealth that have worked for me and can work for you, too.Long-Term Mindset.

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